[H:20][C@@:21](C)(CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)C#N

[H:23][C@@:22](C)(CC)[C:21]#[N:20].[NH2-:10]>>[H-:23].CC[C@:22](=[C:21]=[N:20][NH2:10])C

[H:14][C:6]([H:15])([H:16])[C:2]([H:12])([H:13])[C@:3]([H:4])([C:7]#[N:8])[C:1]([H:9])([H:10])[H:11].[H:17][N-:5][H:18]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '8\tpi\t7\t2; 3\tsigma\t4\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)C#N 10=20;20,21=21
n_N > π^*_N#C > σ^*_C-H [H:23][C@@:22](C)(CC)[C:21]#[N:20].[NH2-:10]>>[H-:23].CC[C@:22](=[C:21]=[N:20][NH2:10])C 10=20;20,21=21,22;22,23=23
1

CC[C@@H](C)[C:21]#[N:20].[NH2-:10]>>CC[C@@H](C)[C-:21]=[N:20][NH2:10]

[H:14][C:6]([H:15])([H:16])[C:2]([H:12])([H:13])[C@:3]([H:4])([C:7]#[N:8])[C:1]([H:9])([H:10])[H:11].[H:17][N-:5][H:18]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '8\tpi\t7\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)C#N 10=20;20,21=21
n_N > π^*_N#C CC[C@@H](C)[C:21]#[N:20].[NH2-:10]>>CC[C@@H](C)[C-:21]=[N:20][NH2:10] 10=20;20,21=21
1

[H:20][CH2:21][C@H](CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@H]([CH2-:21])C#N

[H:14][C:6]([H:15])([H:16])[C:2]([H:12])([H:13])[C@:3]([H:4])([C:7]#[N:8])[C:1]([H:9])([H:10])[H:11].[H:17][N-:5][H:18]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '9\tsigma\t1\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)C#N 10=20;20,21=21
n_N > σ^*_H-C [H:20][CH2:21][C@H](CC)C#N.[NH2-:10]>>[H:20][NH2:10].CC[C@@H]([CH2-:21])C#N 10=20;20,21=21
1

[H:20][C@@:21](C)(CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)[N+](=O)[O-]

[H:23][C@@:22](C)(CC)[N+:21](=[O:20])[O-].[NH2-:10]>>[H-:23].CC[C@:22](=[N+:21]([O-])[O:20][NH2:10])C

[H:15][C:6]([H:16])([H:17])[C:2]([H:13])([H:14])[C@@:3]([H:4])([C:1]([H:10])([H:11])[H:12])[N+:7](=[O:8])[O-:9].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '8\tpi\t7\t2; 3\tsigma\t4\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)[N+](=O)[O-] 10=20;20,21=21
n_N > π^*_O=N > σ^*_C-H [H:23][C@@:22](C)(CC)[N+:21](=[O:20])[O-].[NH2-:10]>>[H-:23].CC[C@:22](=[N+:21]([O-])[O:20][NH2:10])C 10=20;20,21=21,22;22,23=23
4

[H:20][CH2:21][C@H](CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@H]([CH2-:21])[N+](=O)[O-]

[H:15][C:6]([H:16])([H:17])[C:2]([H:13])([H:14])[C@@:3]([H:4])([C:1]([H:10])([H:11])[H:12])[N+:7](=[O:8])[O-:9].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '10\tsigma\t1\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)[N+](=O)[O-] 10=20;20,21=21
n_N > σ^*_H-C [H:20][CH2:21][C@H](CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@H]([CH2-:21])[N+](=O)[O-] 10=20;20,21=21
4

[H:20][CH2:21]C[C@@H](C)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].C[C@H](C[CH2-:21])[N+](=O)[O-]

[H:15][C:6]([H:16])([H:17])[C:2]([H:13])([H:14])[C@@:3]([H:4])([C:1]([H:10])([H:11])[H:12])[N+:7](=[O:8])[O-:9].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '15\tsigma\t6\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)[N+](=O)[O-] 10=20;20,21=21
n_N > σ^*_H-C [H:20][CH2:21]C[C@@H](C)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].C[C@H](C[CH2-:21])[N+](=O)[O-] 10=20;20,21=21
4

[H:10][CH2:11][C@:21]([H:20])(CC)[N+](=O)[O-].[NH2-]>>[H:20][H:10].CC[C@@-:21]([CH2+:11])[N+](=O)[O-].[NH2-]

[H:15][C:6]([H:16])([H:17])[C:2]([H:13])([H:14])[C@@:3]([H:4])([C:1]([H:10])([H:11])[H:12])[N+:7](=[O:8])[O-:9].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('10\tsigma\t1\t2', '4\tsigma\t3\t2')
n_N > σ^*_H-C [H:20][C@@:21](C)(CC)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].CC[C@@-:21](C)[N+](=O)[O-] 10=20;20,21=21
σ_H-C > σ^*_H-C [H:10][CH2:11][C@:21]([H:20])(CC)[N+](=O)[O-].[NH2-]>>[H:20][H:10].CC[C@@-:21]([CH2+:11])[N+](=O)[O-].[NH2-] 10,11=10,20;20,21=21
4

C1=C[C:20](=[N:21]C=C1)Cl.[NH2-:10]>>C1=C[C:20]([N-:21]C=C1)([NH2:10])Cl

[H:20][C:21]1=[CH:22][CH:23]=CN=C1Cl.[NH2-:10]>>[H:20][NH2:10].[CH-:23]=CN=C([C:21]#[CH:22])Cl

[H:8][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[Cl:7])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '9\tsigma\t4\t2; 3\tsigma\t6\t2')
n_N > π^*_C=N C1=C[C:20](=[N:21]C=C1)Cl.[NH2-:10]>>C1=C[C:20]([N-:21]C=C1)([NH2:10])Cl 10=20;20,21=21
n_N > σ^*_H-C > σ^*_C-C [H:20][C:21]1=[CH:22][CH:23]=CN=C1Cl.[NH2-:10]>>[H:20][NH2:10].[CH-:23]=CN=C([C:21]#[CH:22])Cl 10=20;20,21=21,22;22,23=23
7

[H:21][C:20]1=CN=C(C=C1)Cl.[NH2-:10]>>[H-:21].C1=CC(=NC=[C:20]1[NH2:10])Cl

[H:8][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[Cl:7])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '6\tsigma\t12\t2')
n_N > π^*_C=N C1=C[C:20](=[N:21]C=C1)Cl.[NH2-:10]>>C1=C[C:20]([N-:21]C=C1)([NH2:10])Cl 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=CN=C(C=C1)Cl.[NH2-:10]>>[H-:21].C1=CC(=NC=[C:20]1[NH2:10])Cl 10=20;20,21=21
7

C1=CC(=NC=C1)Cl.C1=C[C:20](=[N:21]C=C1)Cl.[NH2-:10]>>C1=CC(=NC=C1)Cl.C1=C[C:20]([N-:21]C=C1)([NH2:10])Cl

C1=C[C:10](=[N:11]C=C1)Cl.C1=C[C:20](=[N:21]C=C1)Cl.[NH2-]>>C1=C[C:20]([N-:21]C=C1)([C:10]2(C=CC=C[N+:11]2)Cl)Cl.[NH2-]

[H:10008][C:10003]1=[C:10004]([C:10001](=[N:10002][C:10005](=[C:10006]1[H:10012])[H:10011])[Cl:10007])[H:10009].[H:8][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[Cl:7])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10001\tpi\t10002\t2', '1\tpi\t2\t2')
n_N > π^*_C=N C1=CC(=NC=C1)Cl.C1=C[C:20](=[N:21]C=C1)Cl.[NH2-:10]>>C1=CC(=NC=C1)Cl.C1=C[C:20]([N-:21]C=C1)([NH2:10])Cl 10=20;20,21=21
π_C=N > π^*_C=N C1=C[C:10](=[N:11]C=C1)Cl.C1=C[C:20](=[N:21]C=C1)Cl.[NH2-]>>C1=C[C:20]([N-:21]C=C1)([C:10]2(C=CC=C[N+:11]2)Cl)Cl.[NH2-] 10,11=10,20;20,21=21
9

C1=C[C@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@@:20](=[N:10]C=C1)N.[Cl-:21]

[H:20][C:21]1=C[N-:10][C@@](C=C1)(N)Cl>>[H:20][N:10]1C=[C-:21]C=C[C@]1(N)Cl

[H:8][C:3]1=[C:4]([C@:1]([N-:2][C:5](=[C:6]1[H:12])[H:11])([N:7]([H:13])[H:14])[Cl:10])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '12\tsigma\t6\t2')
n_N > σ^*_C-Cl C1=C[C@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@@:20](=[N:10]C=C1)N.[Cl-:21] 10=20;20,21=21
n_N > σ^*_H-C [H:20][C:21]1=C[N-:10][C@@](C=C1)(N)Cl>>[H:20][N:10]1C=[C-:21]C=C[C@]1(N)Cl 10=20;20,21=21
10

[H:20][NH:21][C@@]1(C=CC=C[N-:10]1)Cl>>[H:20][N:10]1C=CC=C[C@]1([NH-:21])Cl

[H:8][C:3]1=[C:4]([C@:1]([N-:2][C:5](=[C:6]1[H:12])[H:11])([N:7]([H:13])[H:14])[Cl:10])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '13\tsigma\t7\t2')
n_N > σ^*_C-Cl C1=C[C@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@@:20](=[N:10]C=C1)N.[Cl-:21] 10=20;20,21=21
n_N > σ^*_H-N [H:20][NH:21][C@@]1(C=CC=C[N-:10]1)Cl>>[H:20][N:10]1C=CC=C[C@]1([NH-:21])Cl 10=20;20,21=21
10

[H:21][C:20]1=C[C@@]([N-:10]C=C1)(N)Cl>>[H-:21].C1=C[N:10]2[C:20]1=C[C@@]2(N)Cl

[H:8][C:3]1=[C:4]([C@@:1]([N-:2][C:5](=[C:6]1[H:12])[H:11])([N:7]([H:13])[H:14])[Cl:10])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '3\tsigma\t8\t2')
n_N > σ^*_C-Cl C1=C[C@@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@:20](=[N:10]C=C1)N.[Cl-:21] 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=C[C@@]([N-:10]C=C1)(N)Cl>>[H-:21].C1=C[N:10]2[C:20]1=C[C@@]2(N)Cl 10=20;20,21=21
13

[H:20][C:21]1=[C:22]([N-:10][C@](C=C1)(N)Cl)[H:23]>>[H-:23].[H:20][N:10]1[C:22]#[C:21]C=C[C@@]1(N)Cl

[H:8][C:3]1=[C:4]([C@@:1]([N-:2][C:5](=[C:6]1[H:12])[H:11])([N:7]([H:13])[H:14])[Cl:10])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '12\tsigma\t6\t2; 5\tsigma\t11\t2')
n_N > σ^*_C-Cl C1=C[C@@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@:20](=[N:10]C=C1)N.[Cl-:21] 10=20;20,21=21
n_N > σ^*_H-C > σ^*_C-H [H:20][C:21]1=[C:22]([N-:10][C@](C=C1)(N)Cl)[H:23]>>[H-:23].[H:20][N:10]1[C:22]#[C:21]C=C[C@@]1(N)Cl 10=20;20,21=21,22;22,23=23
13

[H:8][C:3]1=[C:4]([C@@:1]([N-:2][C:5](=[C:6]1[H:12])[H:11])([N:7]([H:13])[H:14])[Cl:10])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '13\tsigma\t7\t2')
n_N > σ^*_C-Cl C1=C[C@@:20]([N-:10]C=C1)(N)[Cl:21]>>C1=C[C@:20](=[N:10]C=C1)N.[Cl-:21] 10=20;20,21=21
n_N > σ^*_H-N [H:20][NH:21][C@]1(C=CC=C[N-:10]1)Cl>>[H:20][N:10]1C=CC=C[C@@]1([NH-:21])Cl 10=20;20,21=21
13

[H:20][C:21]1=[C:22](C=NC=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:22]#[C:21]1.[Cl-:23]

[H:20][C:21]1=[CH:22][N:23]=CC(=C1)Cl.[NH2-:10]>>[H:20][NH2:10].[CH:22]#[C:21]C=C(C=[N-:23])Cl

[H:10][C:6]1=[C:7]([N:8]=[C:9]([C:2](=[C:1]1[H:3])[Cl:4])[H:12])[H:11].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '10\tsigma\t6\t2; 7\tsigma\t8\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=NC=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:22]#[C:21]1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-N [H:20][C:21]1=[CH:22][N:23]=CC(=C1)Cl.[NH2-:10]>>[H:20][NH2:10].[CH:22]#[C:21]C=C(C=[N-:23])Cl 10=20;20,21=21,22;22,23=23
16

C1=C[N:21]=[CH:20]C(=C1)Cl.[NH2-:10]>>C1=C[N-:21][CH:20](C(=C1)Cl)[NH2:10]

[H:10][C:6]1=[C:7]([N:8]=[C:9]([C:2](=[C:1]1[H:3])[Cl:4])[H:12])[H:11].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '9\tpi\t8\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=NC=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:22]#[C:21]1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C=N C1=C[N:21]=[CH:20]C(=C1)Cl.[NH2-:10]>>C1=C[N-:21][CH:20](C(=C1)Cl)[NH2:10] 10=20;20,21=21
16

C1=C[N:23]=[CH:22][C:21](=[CH:20]1)Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[C:21]([CH:20]1[NH2:10])Cl

[H:10][C:6]1=[C:7]([N:8]=[C:9]([C:2](=[C:1]1[H:3])[Cl:4])[H:12])[H:11].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '1\tpi\t2\t2; 9\tpi\t8\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=NC=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:22]#[C:21]1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][C:21](=[CH:20]1)Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[C:21]([CH:20]1[NH2:10])Cl 10=20;20,21=21,22;22,23=23
16

[H:20][C:21]1=[C:22]([CH:13]=[N:12][CH:11]=[CH:10]1)[Cl:23].[NH2-]>>[H:20][CH:10]1[CH:11]=[N:12][CH+:13][C:22]#[C:21]1.[NH2-].[Cl-:23]

[H:10][C:6]1=[C:7]([N:8]=[C:9]([C:2](=[C:1]1[H:3])[Cl:4])[H:12])[H:11].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('6\tpi\t7\t2; 8\tpi\t9\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=NC=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:22]#[C:21]1.[Cl-:23] 10=20;20,21=21,22;22,23=23
π_N=C > π_C=C > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22]([CH:13]=[N:12][CH:11]=[CH:10]1)[Cl:23].[NH2-]>>[H:20][CH:10]1[CH:11]=[N:12][CH+:13][C:22]#[C:21]1.[NH2-].[Cl-:23] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
16

[H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23]

[H:10][C:11]1=N[C:21](=[C:22](C=C1)[Cl:23])[H:20].[NH2-]>>[H:10][H:20].C1=C[C+:11]=N[C:21]#[C:22]1.[NH2-].[Cl-:23]

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('12\tsigma\t8\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > σ^*_C-Cl [H:10][C:11]1=N[C:21](=[C:22](C=C1)[Cl:23])[H:20].[NH2-]>>[H:10][H:20].C1=C[C+:11]=N[C:21]#[C:22]1.[NH2-].[Cl-:23] 10,11=10,20;20,21=21,22;22,23=23
19

C1=[CH:21][C:20](=CN=C1)Cl.[NH2-:10]>>[CH-:21]=CC=NC=[C:20]([NH2:10])Cl

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '2\tsigma\t6\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-C C1=[CH:21][C:20](=CN=C1)Cl.[NH2-:10]>>[CH-:21]=CC=NC=[C:20]([NH2:10])Cl 10=20;20,21=21
25

[H:20][C:21]1=[CH:22][CH:23]=NC=C1Cl.[NH2-:10]>>[H:20][NH2:10].[CH-:23]=NC=C([C:21]#[CH:22])Cl

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '10\tsigma\t6\t2; 7\tsigma\t8\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-C [H:20][C:21]1=[CH:22][CH:23]=NC=C1Cl.[NH2-:10]>>[H:20][NH2:10].[CH-:23]=NC=C([C:21]#[CH:22])Cl 10=20;20,21=21,22;22,23=23
25

[H:21][C:20]1=CC(=CN=C1)Cl.[NH2-:10]>>[H-:21].C1=[C:20](C=NC=C1Cl)[NH2:10]

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '7\tsigma\t11\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-H [H:21][C:20]1=CC(=CN=C1)Cl.[NH2-:10]>>[H-:21].C1=[C:20](C=NC=C1Cl)[NH2:10] 10=20;20,21=21
25

[H:20][C:21]1=CC(=C[N:23]=[CH:22]1)Cl.[NH2-:10]>>[H:20][NH2:10].C1=[C:21]=[CH:22][N-:23]C=C1Cl

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('5\tsp3\tNone\t2', '11\tsigma\t7\t2; 8\tpi\t9\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > π^*_C=N [H:20][C:21]1=CC(=C[N:23]=[CH:22]1)Cl.[NH2-:10]>>[H:20][NH2:10].C1=[C:21]=[CH:22][N-:23]C=C1Cl 10=20;20,21=21,22;22,23=23
25

[H:20][C:21]1=[C:22]([CH:10]=[CH:11]C=N1)[Cl:23].[NH2-]>>[H:20][CH:10]1[CH+:11]C=N[C:21]#[C:22]1.[NH2-].[Cl-:23]

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('6\tpi\t7\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
π_C=C > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22]([CH:10]=[CH:11]C=N1)[Cl:23].[NH2-]>>[H:20][CH:10]1[CH+:11]C=N[C:21]#[C:22]1.[NH2-].[Cl-:23] 10,11=10,20;20,21=21,22;22,23=23
25

[H:10][C:11]1=CC=N[C:21](=[C:22]1[Cl:23])[H:20].[NH2-]>>[H:20][H:10].C1=[C+:11][C:22]#[C:21]N=C1.[NH2-].[Cl-:23]

[H:11][C:7]1=[C:6]([C:2](=[C:1]([N:9]=[C:8]1[H:12])[H:3])[Cl:4])[H:10].[H:13][N-:5][H:14]
('5\tsp3\tNone\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2') ('10\tsigma\t6\t2', '3\tsigma\t1\t2; 2\tsigma\t4\t2')
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CC=N1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=C[C:22]#[C:21]N=C1.[Cl-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > σ^*_C-Cl [H:10][C:11]1=CC=N[C:21](=[C:22]1[Cl:23])[H:20].[NH2-]>>[H:20][H:10].C1=[C+:11][C:22]#[C:21]N=C1.[NH2-].[Cl-:23] 10,11=10,20;20,21=21,22;22,23=23
25

[H:21][C:20]1=NC=CC#C1.[NH2-:10]>>[H-:21].C1=CN=[C:20](C#C1)[NH2:10]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:1]#[C:2]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '6\tsigma\t9\t2')
n_N > π^*_C#C C1=CN=C[C:21]#[C:20]1.[NH2-:10]>>C1=CN=C[C-:21]=[C:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=NC=CC#C1.[NH2-:10]>>[H-:21].C1=CN=[C:20](C#C1)[NH2:10] 10=20;20,21=21
28

[CH:10]1=[CH:11]N=C[C:21]#[C:20]1.[NH2-]>>[CH:10]1=[C:20]=[C-:21]C=N[CH+:11]1.[NH2-]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:1]#[C:2]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('3\tpi\t4\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=C[C:21]#[C:20]1.[NH2-:10]>>C1=CN=C[C-:21]=[C:20]1[NH2:10] 10=20;20,21=21
π_C=C > π^*_C#C [CH:10]1=[CH:11]N=C[C:21]#[C:20]1.[NH2-]>>[CH:10]1=[C:20]=[C-:21]C=N[CH+:11]1.[NH2-] 10,11=10,20;20,21=21
28

[H:11][C:10]1=CN=C[C:20]#[C:21]1.[NH2-]>>[H+:11].C1=[C:10]2[C-:21]=[C:20]2C=N1.[NH2-]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:2]#[C:1]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('3\tsigma\t7\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=C[C:20]#[C:21]1.[NH2-:10]>>C1=CN=C[C:20](=[C-:21]1)[NH2:10] 10=20;20,21=21
σ_C-H > π^*_C#C [H:11][C:10]1=CN=C[C:20]#[C:21]1.[NH2-]>>[H+:11].C1=[C:10]2[C-:21]=[C:20]2C=N1.[NH2-] 10,11=10,20;20,21=21
31

[H:11][C:10]1=NC=C[C:21]#[C:20]1.[NH2-]>>[H+:11].C1=CN=[C:10]=[C:20]=[C-:21]1.[NH2-]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:2]#[C:1]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('6\tsigma\t9\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=C[C:20]#[C:21]1.[NH2-:10]>>C1=CN=C[C:20](=[C-:21]1)[NH2:10] 10=20;20,21=21
σ_C-H > π^*_C#C [H:11][C:10]1=NC=C[C:21]#[C:20]1.[NH2-]>>[H+:11].C1=CN=[C:10]=[C:20]=[C-:21]1.[NH2-] 10,11=10,20;20,21=21
31

C1=CN=CC#C1.C1=CN=C[C:20]#[C:21]1.[NH2-:10]>>C1=CN=C[C:20](=[C-:21]1)[NH2:10].C1=CN=CC#C1

[CH:11]1=CN=CC#[C:10]1.C1=CN=C[C:20]#[C:21]1.[NH2-]>>[CH+:11]=CN=CC#[C:10][C:20]1=[C-:21]C=CN=C1.[NH2-]

[H:10007][C:10003]1=[C:10004]([N:10005]=[C:10006]([C:10002]#[C:10001]1)[H:10009])[H:10008].[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:2]#[C:1]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('10001\tsigma\t10003\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=CC#C1.C1=CN=C[C:20]#[C:21]1.[NH2-:10]>>C1=CN=C[C:20](=[C-:21]1)[NH2:10].C1=CN=CC#C1 10=20;20,21=21
σ_C-C > π^*_C#C [CH:11]1=CN=CC#[C:10]1.C1=CN=C[C:20]#[C:21]1.[NH2-]>>[CH+:11]=CN=CC#[C:10][C:20]1=[C-:21]C=CN=C1.[NH2-] 10,11=10,20;20,21=21
32

[CH:22]1=[CH:23]N=C[C:20]#[C:21]1.[NH2-:10]>>[CH-:23]1[CH:22]=[C:21]=[C:20](C=N1)[NH2:10]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:1]#[C:2]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2')
n_N > π^*_C#C C1=CN=C[C:21]#[C:20]1.[NH2-:10]>>C1=CN=C[C-:21]=[C:20]1[NH2:10] 10=20;20,21=21
n_N > π^*_C#C > π^*_C=C [CH:22]1=[CH:23]N=C[C:20]#[C:21]1.[NH2-:10]>>[CH-:23]1[CH:22]=[C:21]=[C:20](C=N1)[NH2:10] 10=20;20,21=21,22;22,23=23
33

[CH:13]1=[CH:12][N:11]=[CH:10][C:21]#[C:20]1.[NH2-]>>[CH:12]1=[N:11][CH:10]2[C-:21]=[C:20]2[CH+:13]1.[NH2-]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:1]#[C:2]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('6\tpi\t5\t2; 4\tpi\t3\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=C[C:21]#[C:20]1.[NH2-:10]>>C1=CN=C[C-:21]=[C:20]1[NH2:10] 10=20;20,21=21
π_C=C > π_C=N > π^*_C#C [CH:13]1=[CH:12][N:11]=[CH:10][C:21]#[C:20]1.[NH2-]>>[CH:12]1=[N:11][CH:10]2[C-:21]=[C:20]2[CH+:13]1.[NH2-] 10,11=10,20;12,13=11,12;20,21=21
33

[CH:10]1=[CH:11][N:12]=C[C:21]#[C:20]1.[NH2-]>>[CH:10]1=[C:20]=[C-:21]C=[N+:12]=[CH:11]1.[NH2-]

[H:7][C:3]1=[C:4]([N:5]=[C:6]([C:1]#[C:2]1)[H:9])[H:8].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('3\tpi\t4\t2; 5\tsp2\tNone\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CN=C[C:21]#[C:20]1.[NH2-:10]>>C1=CN=C[C-:21]=[C:20]1[NH2:10] 10=20;20,21=21
n_N > π_C=C > π^*_C#C [CH:10]1=[CH:11][N:12]=C[C:21]#[C:20]1.[NH2-]>>[CH:10]1=[C:20]=[C-:21]C=[N+:12]=[CH:11]1.[NH2-] 10,11=10,20;12=11;20,21=21
33

[H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21]

[H:20][C:21]1=CC(=[C-:10][CH:23]=[N:22]1)N.N>>[H:20][C:10]1=C(C=[C:21]=[N:22][CH-:23]1)N.N

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '12\tsigma\t4\t2; 5\tpi\t6\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_H-C > π^*_N=C [H:20][C:21]1=CC(=[C-:10][CH:23]=[N:22]1)N.N>>[H:20][C:10]1=C(C=[C:21]=[N:22][CH-:23]1)N.N 10=20;20,21=21,22;22,23=23
38

C1=CN=C[C-:10]=[C:20]1[NH2:21].N>>C1=CN=C[C:10]#[C:20]1.N.[NH2-:21]

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '7\tsigma\t8\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_C-N C1=CN=C[C-:10]=[C:20]1[NH2:21].N>>C1=CN=C[C:10]#[C:20]1.N.[NH2-:21] 10=20;20,21=21
38

[CH:21]1=[CH:20]N=C[C-:10]=[C:22]1[NH2:23].N>>[CH:21]1=[C:22]=[C:10]2[CH:20]1N=C2.N.[NH2-:23]

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '4\tpi\t3\t2; 7\tsigma\t8\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
n_C > π^*_C=C > σ^*_C-N [CH:21]1=[CH:20]N=C[C-:10]=[C:22]1[NH2:23].N>>[CH:21]1=[C:22]=[C:10]2[CH:20]1N=C2.N.[NH2-:23] 10=20;20,21=21,22;22,23=23
38

[H:20][NH2:21].[CH:10]1=[CH:11][N:12]=[CH:13][C-]=C1N>>[H:20][CH:10]1[CH:11]=[N:12][CH+:13][C-]=C1N.[NH2-:21]

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('3\tpi\t4\t2; 5\tpi\t6\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
π_N=C > π_C=C > σ^*_H-N [H:20][NH2:21].[CH:10]1=[CH:11][N:12]=[CH:13][C-]=C1N>>[H:20][CH:10]1[CH:11]=[N:12][CH+:13][C-]=C1N.[NH2-:21] 10,11=10,20;12,13=11,12;20,21=21
38

[H:20][NH2:21].[CH:10]1=[CH:11][N:12]=C[C-]=C1N>>[H:20][CH:10]1[CH:11]=[N+:12]=C[C-]=C1N.[NH2-:21]

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('3\tpi\t4\t2; 5\tsp2\tNone\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
n_N > π_C=C > σ^*_H-N [H:20][NH2:21].[CH:10]1=[CH:11][N:12]=C[C-]=C1N>>[H:20][CH:10]1[CH:11]=[N+:12]=C[C-]=C1N.[NH2-:21] 10,11=10,20;12=11;20,21=21
38

[H:20][NH2:21].C1=CN=C[C-]=[C:11]1[NH2:10]>>[H:20][NH2:10].C1=CN=C[C-]=[C+:11]1.[NH2-:21]

[H:13][C:6]1=[N:5][C:4](=[C:3]([C:7](=[C-:1]1)[N:8]([H:14])[H:15])[H:11])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('8\tsigma\t7\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-:10]=C1N>>[H:20][C:10]1=C(C=CN=C1)N.[NH2-:21] 10=20;20,21=21
σ_N-C > σ^*_H-N [H:20][NH2:21].C1=CN=C[C-]=[C:11]1[NH2:10]>>[H:20][NH2:10].C1=CN=C[C-]=[C+:11]1.[NH2-:21] 10,11=10,20;20,21=21
38

[H:20][NH2:21].C1=[C-:10]C(=CN=C1)N>>[H:20][C:10]1=CC=NC=C1N.[NH2-:21]

[H:21][C:20]1=[C-:10]C(=CN=C1)N.N>>[H-:21].C1=NC=C([C:10]#[C:20]1)N.N

[H:11][C:3]1=[C-:1][C:7](=[C:6]([N:5]=[C:4]1[H:12])[H:13])[N:8]([H:14])[H:15].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '3\tsigma\t11\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=[C-:10]C(=CN=C1)N>>[H:20][C:10]1=CC=NC=C1N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_C-H [H:21][C:20]1=[C-:10]C(=CN=C1)N.N>>[H-:21].C1=NC=C([C:10]#[C:20]1)N.N 10=20;20,21=21
41

[H:20][C:21]1=C([C-:10]=CC=N1)N.N>>[H:20][C:10]1=CC=N[C-:21]=C1N.N

[H:11][C:3]1=[C-:1][C:7](=[C:6]([N:5]=[C:4]1[H:12])[H:13])[N:8]([H:14])[H:15].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '13\tsigma\t6\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=[C-:10]C(=CN=C1)N>>[H:20][C:10]1=CC=NC=C1N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_H-C [H:20][C:21]1=C([C-:10]=CC=N1)N.N>>[H:20][C:10]1=CC=N[C-:21]=C1N.N 10=20;20,21=21
41

[CH:20]1=CC#CN=[CH:21]1.[NH2-:10]>>[CH-:21]=NC#CC=[CH:20][NH2:10]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '3\tsigma\t6\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_C-C [CH:20]1=CC#CN=[CH:21]1.[NH2-:10]>>[CH-:21]=NC#CC=[CH:20][NH2:10] 10=20;20,21=21
44

[CH:20]1=[CH:21][C:22]#[C:23]N=C1.[NH2-:10]>>[CH:21]1=[C:22]=[C-:23]N=C[CH:20]1[NH2:10]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '3\tpi\t4\t2; 1\tpi\t2\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
n_N > π^*_C=C > π^*_C#C [CH:20]1=[CH:21][C:22]#[C:23]N=C1.[NH2-:10]>>[CH:21]1=[C:22]=[C-:23]N=C[CH:20]1[NH2:10] 10=20;20,21=21,22;22,23=23
44

[H:21][C:20]1=NC#CC=C1.[NH2-:10]>>[H-:21].C1=C[C:20](=NC#C1)[NH2:10]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '6\tsigma\t9\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=NC#CC=C1.[NH2-:10]>>[H-:21].C1=C[C:20](=NC#C1)[NH2:10] 10=20;20,21=21
44

C1=CC#CN=C1.C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10].C1=CC#CN=C1

C1=C[C:10]#[C:11]N=C1.C1=C[C:21]#[C:20]N=C1.[NH2-]>>C1=C[C-:21]=[C:20](N=C1)[C:10]2=[C+:11]N=CC=C2.[NH2-]

[H:10008][C:10004]1=[C:10003]([C:10006](=[N:10005][C:10002]#[C:10001]1)[H:10009])[H:10007].[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('10001\tpi\t10002\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CC#CN=C1.C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10].C1=CC#CN=C1 10=20;20,21=21
π_C#C > π^*_C#C C1=C[C:10]#[C:11]N=C1.C1=C[C:21]#[C:20]N=C1.[NH2-]>>C1=C[C-:21]=[C:20](N=C1)[C:10]2=[C+:11]N=CC=C2.[NH2-] 10,11=10,20;20,21=21
46

[H:10][C:11]1=N[C:21]#[C:20]C=C1.[NH2-]>>[H:10][C:20]1=[C-:21]N=[C+:11]C=C1.[NH2-]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:1]#[C:2]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('9\tsigma\t6\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=C[C:20]#[C:21]N=C1.[NH2-:10]>>C1=C[C:20](=[C-:21]N=C1)[NH2:10] 10=20;20,21=21
σ_H-C > π^*_C#C [H:10][C:11]1=N[C:21]#[C:20]C=C1.[NH2-]>>[H:10][C:20]1=[C-:21]N=[C+:11]C=C1.[NH2-] 10,11=10,20;20,21=21
47

C1=CC#CN=C1.C1=C[C:20]#[C:21]N=C1.[NH2-:10]>>C1=CC#CN=C1.C1=C[C:20](=[C-:21]N=C1)[NH2:10]

[CH:10]1=[CH:11][C:12]#[C:13]N=C1.C1=C[C:20]#[C:21]N=C1.[NH2-]>>C1=C[C:20](=[C-:21]N=C1)[CH:10]2[CH:11]=[C:12]=[C+:13]N=C2.[NH2-]

[H:10008][C:10004]1=[C:10003]([C:10006](=[N:10005][C:10001]#[C:10002]1)[H:10009])[H:10007].[H:8][C:4]1=[C:3]([C:6](=[N:5][C:1]#[C:2]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('10003\tpi\t10004\t2; 10002\tpi\t10001\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CC#CN=C1.C1=C[C:20]#[C:21]N=C1.[NH2-:10]>>C1=CC#CN=C1.C1=C[C:20](=[C-:21]N=C1)[NH2:10] 10=20;20,21=21
π_C#C > π_C=C > π^*_C#C [CH:10]1=[CH:11][C:12]#[C:13]N=C1.C1=C[C:20]#[C:21]N=C1.[NH2-]>>C1=C[C:20](=[C-:21]N=C1)[CH:10]2[CH:11]=[C:12]=[C+:13]N=C2.[NH2-] 10,11=10,20;12,13=11,12;20,21=21
48

C1=CC#[C:20][N:21]=C1.[NH2-:10]>>C(=CC#[C:20][NH2:10])C=[N-:21]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('11\tsp3\tNone\t2', '2\tsigma\t5\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_C-N C1=CC#[C:20][N:21]=C1.[NH2-:10]>>C(=CC#[C:20][NH2:10])C=[N-:21] 10=20;20,21=21
49

C1=C[C:21]#[C:20][N:10]=[CH:11]1.[NH2-]>>C1=C[C-:21]=[C:20]=[N:10][CH+:11]1.[NH2-]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('5\tpi\t6\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
π_N=C > π^*_C#C C1=C[C:21]#[C:20][N:10]=[CH:11]1.[NH2-]>>C1=C[C-:21]=[C:20]=[N:10][CH+:11]1.[NH2-] 10,11=10,20;20,21=21
49

[H:13][C:12]1=N[C:20]#[C:21][CH:10]=[CH:11]1.[NH2-]>>[H+:13].[CH:11]1=[C:12]=N[C:20]2=[C-:21][CH:10]21.[NH2-]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('4\tpi\t3\t2; 6\tsigma\t9\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10] 10=20;20,21=21
σ_C-H > π_C=C > π^*_C#C [H:13][C:12]1=N[C:20]#[C:21][CH:10]=[CH:11]1.[NH2-]>>[H+:13].[CH:11]1=[C:12]=N[C:20]2=[C-:21][CH:10]21.[NH2-] 10,11=10,20;12,13=11,12;20,21=21
49

C1=C[C:11]#[C:10]N=C1.C1=C[C:21]#[C:20]N=C1.[NH2-]>>C1=C[C-:21]=[C:20](N=C1)[C:10]2=[C+:11]C=CC=N2.[NH2-]

[H:10008][C:10004]1=[C:10003]([C:10006](=[N:10005][C:10002]#[C:10001]1)[H:10009])[H:10007].[H:8][C:4]1=[C:3]([C:6](=[N:5][C:2]#[C:1]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('10002\tpi\t10001\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=CC#CN=C1.C1=C[C:21]#[C:20]N=C1.[NH2-:10]>>C1=C[C-:21]=[C:20](N=C1)[NH2:10].C1=CC#CN=C1 10=20;20,21=21
π_C#C > π^*_C#C C1=C[C:11]#[C:10]N=C1.C1=C[C:21]#[C:20]N=C1.[NH2-]>>C1=C[C-:21]=[C:20](N=C1)[C:10]2=[C+:11]C=CC=N2.[NH2-] 10,11=10,20;20,21=21
51

[H:11][C:10]1=C[C:20]#[C:21]N=C1.[NH2-]>>[H+:11].C1=[C:10]2[C:20]1=[C-:21]N=C2.[NH2-]

[H:8][C:4]1=[C:3]([C:6](=[N:5][C:1]#[C:2]1)[H:9])[H:7].[H:10][N-:11][H:12]
('11\tsp3\tNone\t2', '2\tpi\t1\t2') ('3\tsigma\t7\t2', '2\tpi\t1\t2')
n_N > π^*_C#C C1=C[C:20]#[C:21]N=C1.[NH2-:10]>>C1=C[C:20](=[C-:21]N=C1)[NH2:10] 10=20;20,21=21
σ_C-H > π^*_C#C [H:11][C:10]1=C[C:20]#[C:21]N=C1.[NH2-]>>[H+:11].C1=[C:10]2[C:20]1=[C-:21]N=C2.[NH2-] 10,11=10,20;20,21=21
52

[H:20][NH2:21].C1=C[C-:10]=C(N=C1)N>>[H:20][C:10]1=C(N=CC=C1)N.[NH2-:21]

[H:20][C:21]1=NC(=[C-:10][CH:23]=[CH:22]1)N.N>>[H:20][C:10]1=C(N=[C:21]=[CH:22][CH-:23]1)N.N

[H:12][C:4]1=[C:3]([C:7](=[N:6][C:5](=[C-:1]1)[N:8]([H:14])[H:15])[H:13])[H:11].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '13\tsigma\t7\t2; 3\tpi\t4\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=C[C-:10]=C(N=C1)N>>[H:20][C:10]1=C(N=CC=C1)N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_H-C > π^*_C=C [H:20][C:21]1=NC(=[C-:10][CH:23]=[CH:22]1)N.N>>[H:20][C:10]1=C(N=[C:21]=[CH:22][CH-:23]1)N.N 10=20;20,21=21,22;22,23=23
54

[H:20][NH2:21].C1=C[C-]=[C:11]([N:10]=C1)N>>[H:20][N:10]=CC=C[C-]=[C+:11]N.[NH2-:21]

[H:12][C:4]1=[C:3]([C:7](=[N:6][C:5](=[C-:1]1)[N:8]([H:14])[H:15])[H:13])[H:11].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('6\tsigma\t5\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=C[C-:10]=C(N=C1)N>>[H:20][C:10]1=C(N=CC=C1)N.[NH2-:21] 10=20;20,21=21
σ_N-C > σ^*_H-N [H:20][NH2:21].C1=C[C-]=[C:11]([N:10]=C1)N>>[H:20][N:10]=CC=C[C-]=[C+:11]N.[NH2-:21] 10,11=10,20;20,21=21
54

[H:20][NH2:21].C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.[NH2-:21]

[H:20][C:21]1=[CH:22][CH:23]=N[C-:10]=C1N.N>>[H:20][C:10](=C([C:21]#[CH:22])N)N=[CH-:23].N

[H:11][C:3]1=[C:4]([C:5](=[C-:1][N:6]=[C:7]1[H:13])[N:8]([H:14])[H:15])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '12\tsigma\t4\t2; 3\tsigma\t7\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.[NH2-:21] 10=20;20,21=21
n_C > σ^*_H-C > σ^*_C-C [H:20][C:21]1=[CH:22][CH:23]=N[C-:10]=C1N.N>>[H:20][C:10](=C([C:21]#[CH:22])N)N=[CH-:23].N 10=20;20,21=21,22;22,23=23
57

[H:23][C:22]1=CC(=[C-:10][N:20]=[CH:21]1)N.N>>[H-:23].C1=[C:22]=[CH:21][N:20]=[C:10]=C1N.N

[H:11][C:3]1=[C:4]([C:5](=[C-:1][N:6]=[C:7]1[H:13])[N:8]([H:14])[H:15])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '6\tpi\t7\t2; 3\tsigma\t11\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.[NH2-:21] 10=20;20,21=21
n_C > π^*_N=C > σ^*_C-H [H:23][C:22]1=CC(=[C-:10][N:20]=[CH:21]1)N.N>>[H-:23].C1=[C:22]=[CH:21][N:20]=[C:10]=C1N.N 10=20;20,21=21,22;22,23=23
57

[H:13][C:12]1=CC(=[C-][N:10]=[CH:11]1)N.[H:20][NH2:21]>>[H+:13].[H:20][N:10]1[CH:11]=[C:12]=CC(=[C-]1)N.[NH2-:21]

[H:11][C:3]1=[C:4]([C:5](=[C-:1][N:6]=[C:7]1[H:13])[N:8]([H:14])[H:15])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('6\tpi\t7\t2; 3\tsigma\t11\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.[NH2-:21] 10=20;20,21=21
σ_C-H > π_N=C > σ^*_H-N [H:13][C:12]1=CC(=[C-][N:10]=[CH:11]1)N.[H:20][NH2:21]>>[H+:13].[H:20][N:10]1[CH:11]=[C:12]=CC(=[C-]1)N.[NH2-:21] 10,11=10,20;12,13=11,12;20,21=21
57

[H:20][NH2:21].[CH:11]1=[CH:10]C(=[C-]N=C1)N>>[H:20][CH:10]1[CH+:11]C=N[C-]=C1N.[NH2-:21]

[H:11][C:3]1=[C:4]([C:5](=[C-:1][N:6]=[C:7]1[H:13])[N:8]([H:14])[H:15])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('4\tpi\t3\t2', '2\tsigma\t20\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.[NH2-:21] 10=20;20,21=21
π_C=C > σ^*_H-N [H:20][NH2:21].[CH:11]1=[CH:10]C(=[C-]N=C1)N>>[H:20][CH:10]1[CH+:11]C=N[C-]=C1N.[NH2-:21] 10,11=10,20;20,21=21
57

[H:20][NH2:21].C1=CC(=[C-]N=C1)N.C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.C1=CC(=[C-]N=C1)N.[NH2-:21]

C1=C[C:21](=[C-:20]N=C1)N.C1=CC(=[C-:10]N=C1)N.N>>C1=C[C-:21]([C-:20](N=C1)[C:10]2=C(C=CC=N2)N)N.N

[H:10011][C:10003]1=[C:10004]([C:10005](=[C-:10001][N:10006]=[C:10007]1[H:10013])[N:10008]([H:10014])[H:10015])[H:10012].[H:11][C:3]1=[C:4]([C:5](=[C-:1][N:6]=[C:7]1[H:13])[N:8]([H:14])[H:15])[H:12].[H:2][N:20]([H:9])[H:10]
('1\tsp2\tNone\t2', '2\tsigma\t20\t2') ('1\tsp2\tNone\t2', '10001\tpi\t10005\t2')
n_C > σ^*_H-N [H:20][NH2:21].C1=CC(=[C-]N=C1)N.C1=CC(=[C-:10]N=C1)N>>[H:20][C:10]1=C(C=CC=N1)N.C1=CC(=[C-]N=C1)N.[NH2-:21] 10=20;20,21=21
n_C > π^*_C=C C1=C[C:21](=[C-:20]N=C1)N.C1=CC(=[C-:10]N=C1)N.N>>C1=C[C-:21]([C-:20](N=C1)[C:10]2=C(C=CC=N2)N)N.N 10=20;20,21=21
58

C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl

[H:23][C:22]1=[C:21](N=CC=C1Cl)[H:20].[NH2-:10]>>[H-:23].[H:20][NH2:10].C1=C([C:22]#[C:21]N=C1)Cl

[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('10\tsp3\tNone\t2', '9\tsigma\t6\t2; 5\tsigma\t8\t2')
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-H [H:23][C:22]1=[C:21](N=CC=C1Cl)[H:20].[NH2-:10]>>[H-:23].[H:20][NH2:10].C1=C([C:22]#[C:21]N=C1)Cl 10=20;20,21=21,22;22,23=23
60

C1=[CH:20][N:21]=CC=C1Cl.[NH2-:10]>>C(=[CH:20][NH2:10])C(=CC=[N-:21])Cl

[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('10\tsp3\tNone\t2', '6\tsigma\t4\t2')
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-N C1=[CH:20][N:21]=CC=C1Cl.[NH2-:10]>>C(=[CH:20][NH2:10])C(=CC=[N-:21])Cl 10=20;20,21=21
60

[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('10\tsp3\tNone\t2', '3\tpi\t4\t2')
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
n_N > π^*_C=N C1=C[N:21]=[CH:20]C=C1Cl.[NH2-:10]>>C1=C[N-:21][CH:20](C=C1Cl)[NH2:10] 10=20;20,21=21
60

[H:20][C:21]1=[C:22](C=CN=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:21]#[C:22]1.[Cl-:23]

[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('10\tsp3\tNone\t2', '12\tsigma\t2\t2; 1\tsigma\t7\t2')
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-Cl [H:20][C:21]1=[C:22](C=CN=C1)[Cl:23].[NH2-:10]>>[H:20][NH2:10].C1=CN=C[C:21]#[C:22]1.[Cl-:23] 10=20;20,21=21,22;22,23=23
60

[H:10][C:11]1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-]>>[H:10][C:20]1([CH:21]=[CH:22][N-:23]C=[C+:11]1)Cl.[NH2-]

[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('8\tsigma\t5\t2', '1\tpi\t2\t2; 3\tpi\t4\t2')
n_N > π^*_C=C > π^*_C=N C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
σ_H-C > π^*_C=C > π^*_C=N [H:10][C:11]1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-]>>[H:10][C:20]1([CH:21]=[CH:22][N-:23]C=[C+:11]1)Cl.[NH2-] 10,11=10,20;20,21=21,22;22,23=23
60

C1=CN=CC=C1Cl.C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=CN=CC=C1Cl.C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl

[CH:11]1=[CH:10]N=C[CH:13]=[C:12]1Cl.C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([CH:10]2[CH:11]=[C:12]([CH+:13]C=N2)Cl)Cl.[NH2-]

[H:10008][C:10005]1=[C:10006]([N:10004]=[C:10003]([C:10002](=[C:10001]1[Cl:10007])[H:10012])[H:10011])[H:10009].[H:8][C:5]1=[C:6]([N:4]=[C:3]([C:2](=[C:1]1[Cl:7])[H:12])[H:11])[H:9].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2; 3\tpi\t4\t2') ('10006\tpi\t10005\t2; 10001\tpi\t10002\t2', '1\tpi\t2\t2; 3\tpi\t4\t2')
n_N > π^*_C=C > π^*_C=N C1=CN=CC=C1Cl.C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-:10]>>C1=CN=CC=C1Cl.C1=C[N-:23][CH:22]=[CH:21][C:20]1([NH2:10])Cl 10=20;20,21=21,22;22,23=23
π_C=C > π_C=C > π^*_C=C > π^*_C=N [CH:11]1=[CH:10]N=C[CH:13]=[C:12]1Cl.C1=C[N:23]=[CH:22][CH:21]=[C:20]1Cl.[NH2-]>>C1=C[N-:23][CH:22]=[CH:21][C:20]1([CH:10]2[CH:11]=[C:12]([CH+:13]C=N2)Cl)Cl.[NH2-] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
62

[CH:20]1=[CH:21]C=NC=C1.[NH2-:10]>>[CH-:21]1C=NC=C[CH:20]1[NH2:10]

[H:7][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[H:9])[H:8].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '3\tpi\t4\t2')
n_N > π^*_C=N C1=C[CH:20]=[N:21]C=C1.[NH2-:10]>>C1=C[CH:20]([N-:21]C=C1)[NH2:10] 10=20;20,21=21
n_N > π^*_C=C [CH:20]1=[CH:21]C=NC=C1.[NH2-:10]>>[CH-:21]1C=NC=C[CH:20]1[NH2:10] 10=20;20,21=21
63

[CH:22]1=[CH:23]C=N[CH:20]=[CH:21]1.[NH2-:10]>>[CH-:23]1[CH:22]=[CH:21][CH:20](N=C1)[NH2:10]

[H:7][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[H:9])[H:8].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '5\tpi\t6\t2; 3\tpi\t4\t2')
n_N > π^*_C=N C1=C[CH:20]=[N:21]C=C1.[NH2-:10]>>C1=C[CH:20]([N-:21]C=C1)[NH2:10] 10=20;20,21=21
n_N > π^*_C=C > π^*_C=C [CH:22]1=[CH:23]C=N[CH:20]=[CH:21]1.[NH2-:10]>>[CH-:23]1[CH:22]=[CH:21][CH:20](N=C1)[NH2:10] 10=20;20,21=21,22;22,23=23
63

[H:20][C:21]1=CN=C[CH:23]=[CH:22]1.[NH2-:10]>>[H:20][NH2:10].[CH-:23]1[CH:22]=[C:21]=CN=C1

[H:7][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[H:9])[H:8].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '12\tsigma\t6\t2; 3\tpi\t4\t2')
n_N > π^*_C=N C1=C[CH:20]=[N:21]C=C1.[NH2-:10]>>C1=C[CH:20]([N-:21]C=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > π^*_C=C [H:20][C:21]1=CN=C[CH:23]=[CH:22]1.[NH2-:10]>>[H:20][NH2:10].[CH-:23]1[CH:22]=[C:21]=CN=C1 10=20;20,21=21,22;22,23=23
63

[H:11][C:10]1=CC=C[CH:20]=[N:21]1.[NH2-]>>[H+:11].C1=C[CH:20]2[C:10](=C1)[N-:21]2.[NH2-]

[H:7][C:3]1=[C:4]([C:1](=[N:2][C:5](=[C:6]1[H:12])[H:11])[H:9])[H:8].[H:13][N-:10][H:14]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('5\tsigma\t11\t2', '1\tpi\t2\t2')
n_N > π^*_C=N C1=C[CH:20]=[N:21]C=C1.[NH2-:10]>>C1=C[CH:20]([N-:21]C=C1)[NH2:10] 10=20;20,21=21
σ_C-H > π^*_C=N [H:11][C:10]1=CC=C[CH:20]=[N:21]1.[NH2-]>>[H+:11].C1=C[CH:20]2[C:10](=C1)[N-:21]2.[NH2-] 10,11=10,20;20,21=21
63

[H:21][C:20]1=CC=C[C@H]([N-:10]1)N>>[H-:21].C1=C[C@H]([N:10]=[C:20]=C1)N

[H:9][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '6\tsigma\t12\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC=C[N-:10]1)N>>[H-:21].C1=C[C@:20](=[N:10]C=C1)N 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=CC=C[C@H]([N-:10]1)N>>[H-:21].C1=C[C@H]([N:10]=[C:20]=C1)N 10=20;20,21=21
66

[H:10][C:11]1=CC=C[N-][C@:20]1([H:21])N>>[H-:21].[H:10][C@@:20]1([C+:11]=CC=C[N-]1)N

[H:9][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('8\tsigma\t3\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC=C[N-:10]1)N>>[H-:21].C1=C[C@:20](=[N:10]C=C1)N 10=20;20,21=21
σ_H-C > σ^*_C-H [H:10][C:11]1=CC=C[N-][C@:20]1([H:21])N>>[H-:21].[H:10][C@@:20]1([C+:11]=CC=C[N-]1)N 10,11=10,20;20,21=21
66

[H:21][C@:20]1(C=CC=C[N-:10]1)N.C1=C[C@H]([N-]C=C1)N>>[H-:21].C1=C[C@H]([N-]C=C1)N.C1=C[C@:20](=[N:10]C=C1)N

[H:21][C@:20]1(C=CC=C[N-]1)N.[CH:10]1=[CH:11][C@H:12]([N-:13]C=C1)N>>[H-:21].C1=C[C@:20]([N-]C=C1)([CH:10]([CH:11]=[C@@H:12]N)C=C[N:13])N

[H:10009][C:10004]1=[C:10003]([C@@:10001]([N-:10002][C:10006](=[C:10005]1[H:10011])[H:10012])([H:10010])[N:10007]([H:10013])[H:10014])[H:10008].[H:9][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('10004\tpi\t10003\t2; 10001\tsigma\t10002\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC=C[N-:10]1)N.C1=C[C@H]([N-]C=C1)N>>[H-:21].C1=C[C@H]([N-]C=C1)N.C1=C[C@:20](=[N:10]C=C1)N 10=20;20,21=21
σ_C-N > π_C=C > σ^*_C-H [H:21][C@:20]1(C=CC=C[N-]1)N.[CH:10]1=[CH:11][C@H:12]([N-:13]C=C1)N>>[H-:21].C1=C[C@:20]([N-]C=C1)([CH:10]([CH:11]=[C@@H:12]N)C=C[N:13])N 10,11=10,20;12,13=11,12;20,21=21
68

[H:10][C@:11]1(C=CC=C[N-]1)N.[H:21][C@:20]1(C=CC=C[N-]1)N>>[H-:21].[H:10][C@@:20]1(C=CC=C[N-]1)N.C1=C[C@+:11]([N-]C=C1)N

[H:10009][C:10004]1=[C:10003]([C@@:10001]([N-:10002][C:10006](=[C:10005]1[H:10011])[H:10012])([H:10010])[N:10007]([H:10013])[H:10014])[H:10008].[H:9][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('10010\tsigma\t10001\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC=C[N-:10]1)N.C1=C[C@H]([N-]C=C1)N>>[H-:21].C1=C[C@H]([N-]C=C1)N.C1=C[C@:20](=[N:10]C=C1)N 10=20;20,21=21
σ_H-C > σ^*_C-H [H:10][C@:11]1(C=CC=C[N-]1)N.[H:21][C@:20]1(C=CC=C[N-]1)N>>[H-:21].[H:10][C@@:20]1(C=CC=C[N-]1)N.C1=C[C@+:11]([N-]C=C1)N 10,11=10,20;20,21=21
68

[H:20][C:21]1=CC=C[N-:10][C@@:22]1([H:23])N>>[H-:23].[H:20][N:10]1C=CC=[C:21]=[C@@:22]1N

[H:9][C:4]1=[C:3]([C@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '8\tsigma\t3\t2; 1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C=CC=C[N-:10]1)N>>[H-:21].C1=C[C@@:20](=[N:10]C=C1)N 10=20;20,21=21
n_N > σ^*_H-C > σ^*_C-H [H:20][C:21]1=CC=C[N-:10][C@@:22]1([H:23])N>>[H-:23].[H:20][N:10]1C=CC=[C:21]=[C@@:22]1N 10=20;20,21=21,22;22,23=23
69

[H:23][C:22]1=C[N-:10][C@H]([CH:20]=[CH:21]1)N>>[H-:23].[CH:21]1=[C:22]=C[N:10]2[CH:20]1[C@@H]2N

[H:9][C:4]1=[C:3]([C@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '3\tpi\t4\t2; 5\tsigma\t11\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C=CC=C[N-:10]1)N>>[H-:21].C1=C[C@@:20](=[N:10]C=C1)N 10=20;20,21=21
n_N > π^*_C=C > σ^*_C-H [H:23][C:22]1=C[N-:10][C@H]([CH:20]=[CH:21]1)N>>[H-:23].[CH:21]1=[C:22]=C[N:10]2[CH:20]1[C@@H]2N 10=20;20,21=21,22;22,23=23
69

[H:21][C@@:20]1(C=C[CH:10]=[CH:11][N-]1)N>>[H-:21].C1=C[C@@:20]2([CH:10]1[CH+:11][N-]2)N

[H:9][C:4]1=[C:3]([C@:1]([N-:2][C:6](=[C:5]1[H:11])[H:12])([H:10])[N:7]([H:13])[H:14])[H:8]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('5\tpi\t6\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C=CC=C[N-:10]1)N>>[H-:21].C1=C[C@@:20](=[N:10]C=C1)N 10=20;20,21=21
π_C=C > σ^*_C-H [H:21][C@@:20]1(C=C[CH:10]=[CH:11][N-]1)N>>[H-:21].C1=C[C@@:20]2([CH:10]1[CH+:11][N-]2)N 10,11=10,20;20,21=21
69

[H:20][CH2:21]c1ccccn1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccccn1

[CH3:21][c:20]1ccccn1.[NH2-:10]>>[CH3-:21].c1ccn[c:20](c1)[NH2:10]

[H:13][c:6]1[c:7]([c:8]([n:9][c:1]([c:2]1[H:12])[C:3]([H:4])([H:10])[H:11])[H:15])[H:14].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '1\tsigma\t3\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccccn1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccccn1 10=20;20,21=21
n_N > σ^*_C-C [CH3:21][c:20]1ccccn1.[NH2-:10]>>[CH3-:21].c1ccn[c:20](c1)[NH2:10] 10=20;20,21=21
72

Cc1[cH:20][cH:21]ccn1.[NH2-:10]>>Cc1[cH:20]([cH-:21]ccn1)[NH2:10]

[H:13][c:6]1[c:7]([c:8]([n:9][c:1]([c:2]1[H:12])[C:3]([H:4])([H:10])[H:11])[H:15])[H:14].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '2\tpi\t6\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccccn1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccccn1 10=20;20,21=21
n_N > π^*_C:C Cc1[cH:20][cH:21]ccn1.[NH2-:10]>>Cc1[cH:20]([cH-:21]ccn1)[NH2:10] 10=20;20,21=21
72

Cc1[cH:23][cH:22][cH:21][cH:20]n1.[NH2-:10]>>Cc1[cH-:23][cH:22][cH:21][cH:20](n1)[NH2:10]

[H:13][c:6]1[c:7]([c:8]([n:9][c:1]([c:2]1[H:12])[C:3]([H:4])([H:10])[H:11])[H:15])[H:14].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '8\tpi\t7\t2; 6\tpi\t2\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccccn1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccccn1 10=20;20,21=21
n_N > π^*_C:C > π^*_C:C Cc1[cH:23][cH:22][cH:21][cH:20]n1.[NH2-:10]>>Cc1[cH-:23][cH:22][cH:21][cH:20](n1)[NH2:10] 10=20;20,21=21,22;22,23=23
72

Cc1cc[cH:20][cH:21]n1.[NH2-:10]>>Cc1cc[cH:20]([cH-:21]n1)[NH2:10]

[H:13][c:6]1[c:7]([c:8]([n:9][c:1]([c:2]1[H:12])[C:3]([H:4])([H:10])[H:11])[H:15])[H:14].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '7\tpi\t8\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccccn1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccccn1 10=20;20,21=21
n_N > π^*_C:C Cc1cc[cH:20][cH:21]n1.[NH2-:10]>>Cc1cc[cH:20]([cH-:21]n1)[NH2:10] 10=20;20,21=21
72

CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10]

[H:20][C:21]1=CC=N[CH:23]=[C:22]1C.[NH2-:10]>>[H:20][NH2:10].C[C:22]1=[C:21]=CC=N[CH-:23]1

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '15\tsigma\t7\t2; 4\tpi\t5\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > π^*_C=C [H:20][C:21]1=CC=N[CH:23]=[C:22]1C.[NH2-:10]>>[H:20][NH2:10].C[C:22]1=[C:21]=CC=N[CH-:23]1 10=20;20,21=21,22;22,23=23
75

[H:20][C:21]1=C(C=C[CH:23]=[N:22]1)C.[NH2-:10]>>[H:20][NH2:10].CC1=[C:21]=[N:22][CH-:23]C=C1

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '12\tsigma\t5\t2; 2\tpi\t1\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > π^*_N=C [H:20][C:21]1=C(C=C[CH:23]=[N:22]1)C.[NH2-:10]>>[H:20][NH2:10].CC1=[C:21]=[N:22][CH-:23]C=C1 10=20;20,21=21,22;22,23=23
75

CC1=CN=[CH:20][CH:21]=C1.[NH2-:10]>>CC(=CN=[CH:20][NH2:10])C=[CH-:21]

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '1\tsigma\t6\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_C-C CC1=CN=[CH:20][CH:21]=C1.[NH2-:10]>>CC(=CN=[CH:20][NH2:10])C=[CH-:21] 10=20;20,21=21
75

[H:20][C:21]1=[CH:22][CH:23]=NC=C1C.[NH2-:10]>>[H:20][NH2:10].CC(=CN=[CH-:23])[C:21]#[CH:22]

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '15\tsigma\t7\t2; 6\tsigma\t1\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > σ^*_C-C [H:20][C:21]1=[CH:22][CH:23]=NC=C1C.[NH2-:10]>>[H:20][NH2:10].CC(=CN=[CH-:23])[C:21]#[CH:22] 10=20;20,21=21,22;22,23=23
75

[H:23][C:22]1=CC=N[CH:20]=[C:21]1C.[NH2-:10]>>[H-:23].C[C:21]1=[C:22]=CC=N[CH:20]1[NH2:10]

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '5\tpi\t4\t2; 7\tsigma\t15\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
n_N > π^*_C=C > σ^*_C-H [H:23][C:22]1=CC=N[CH:20]=[C:21]1C.[NH2-:10]>>[H-:23].C[C:21]1=[C:22]=CC=N[CH:20]1[NH2:10] 10=20;20,21=21,22;22,23=23
75

[CH3:10][C:11]1=C[N:21]=[CH:20]C=C1.[NH2-]>>[CH3:10][CH:20]1C=C[C+:11]=C[N-:21]1.[NH2-]

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('3\tsigma\t4\t2', '1\tpi\t2\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
σ_C-C > π^*_C=N [CH3:10][C:11]1=C[N:21]=[CH:20]C=C1.[NH2-]>>[CH3:10][CH:20]1C=C[C+:11]=C[N-:21]1.[NH2-] 10,11=10,20;20,21=21
75

CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10]

[H:20][C:21]1=CN=C[C:23](=[CH:22]1)C.[NH2-:10]>>[H:20][NH2:10].C[C-:23]1[CH:22]=[C:21]=CN=C1

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '13\tsigma\t6\t2; 5\tpi\t4\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > π^*_C=C [H:20][C:21]1=CN=C[C:23](=[CH:22]1)C.[NH2-:10]>>[H:20][NH2:10].C[C-:23]1[CH:22]=[C:21]=CN=C1 10=20;20,21=21,22;22,23=23
78

CC1=[CH:20][CH:21]=CN=C1.[NH2-:10]>>CC(=[CH:20][NH2:10])C=NC=[CH-:21]

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '5\tsigma\t6\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_C-C CC1=[CH:20][CH:21]=CN=C1.[NH2-:10]>>CC(=[CH:20][NH2:10])C=NC=[CH-:21] 10=20;20,21=21
78

CC1=[CH:21][CH:20]=CN=C1.[NH2-:10]>>CC(=[CH-:21])C=NC=[CH:20][NH2:10]

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '6\tsigma\t5\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_C-C CC1=[CH:21][CH:20]=CN=C1.[NH2-:10]>>CC(=[CH-:21])C=NC=[CH:20][NH2:10] 10=20;20,21=21
78

CC1=C[CH:20]=[CH:21]N=C1.[NH2-:10]>>CC1=C[CH:20]([CH-:21]N=C1)[NH2:10]

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '6\tpi\t7\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > π^*_C=C CC1=C[CH:20]=[CH:21]N=C1.[NH2-:10]>>CC1=C[CH:20]([CH-:21]N=C1)[NH2:10] 10=20;20,21=21
78

[H:20][C:21]1=CC=C([CH:23]=[N:22]1)C.[NH2-:10]>>[H:20][NH2:10].CC1=CC=[C:21]=[N:22][CH-:23]1

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '14\tsigma\t7\t2; 2\tpi\t1\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > π^*_N=C [H:20][C:21]1=CC=C([CH:23]=[N:22]1)C.[NH2-:10]>>[H:20][NH2:10].CC1=CC=[C:21]=[N:22][CH-:23]1 10=20;20,21=21,22;22,23=23
78

[H:20][C:21]1=C(C=NC=C1)C.[NH2-:10]>>[H:20][NH2:10].CC1=[C-:21]C=CN=C1

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '12\tsigma\t5\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C [H:20][C:21]1=C(C=NC=C1)C.[NH2-:10]>>[H:20][NH2:10].CC1=[C-:21]C=CN=C1 10=20;20,21=21
78

[H:13][CH2:12][C:11]1=[CH:10][N:21]=[CH:20]C=C1.[NH2-]>>[H+:13].[CH2:12]=[C:11]1C=C[CH:20]2[CH:10]1[N-:21]2.[NH2-]

[H:14][C:6]1=[C:7]([C:4](=[C:5]([N:2]=[C:1]1[H:13])[H:12])[C:3]([H:8])([H:9])[H:11])[H:15].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('5\tpi\t4\t2; 3\tsigma\t8\t2', '1\tpi\t2\t2')
n_N > π^*_C=N CC1=C[N:21]=[CH:20]C=C1.[NH2-:10]>>CC1=C[N-:21][CH:20](C=C1)[NH2:10] 10=20;20,21=21
σ_C-H > π_C=C > π^*_C=N [H:13][CH2:12][C:11]1=[CH:10][N:21]=[CH:20]C=C1.[NH2-]>>[H+:13].[CH2:12]=[C:11]1C=C[CH:20]2[CH:10]1[N-:21]2.[NH2-] 10,11=10,20;12,13=11,12;20,21=21
81

[H:20][C:21]1=CN=CC(=[C:22]1[H:23])C.[NH2-:10]>>[H-:23].[H:20][NH2:10].CC1=[C:22]=[C:21]=CN=C1

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '13\tsigma\t6\t2; 5\tsigma\t12\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > σ^*_C-H [H:20][C:21]1=CN=CC(=[C:22]1[H:23])C.[NH2-:10]>>[H-:23].[H:20][NH2:10].CC1=[C:22]=[C:21]=CN=C1 10=20;20,21=21,22;22,23=23
84

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '6\tpi\t7\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > π^*_C=C CC1=C[CH:20]=[CH:21]N=C1.[NH2-:10]>>CC1=C[CH:20]([CH-:21]N=C1)[NH2:10] 10=20;20,21=21
84

[H:20][C:21]1=[N:22][CH:23]=CC=C1C.[NH2-:10]>>[H:20][NH2:10].CC(=CC=[CH-:23])[C:21]#[N:22]

[H:13][C:6]1=[C:7]([N:2]=[C:1]([C:4](=[C:5]1[H:12])[C:3]([H:8])([H:9])[H:11])[H:15])[H:14].[H:16][N-:10][H:17]
('10\tsp3\tNone\t2', '1\tpi\t2\t2') ('10\tsp3\tNone\t2', '15\tsigma\t1\t2; 2\tsigma\t7\t2')
n_N > π^*_C=N CC1=CC=C[N:21]=[CH:20]1.[NH2-:10]>>CC1=CC=C[N-:21][CH:20]1[NH2:10] 10=20;20,21=21
n_N > σ^*_H-C > σ^*_N-C [H:20][C:21]1=[N:22][CH:23]=CC=C1C.[NH2-:10]>>[H:20][NH2:10].CC(=CC=[CH-:23])[C:21]#[N:22] 10=20;20,21=21,22;22,23=23
84

[H:21][C@@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@:20](C=C1)N

CC1=C[N-:10][C@H]([CH:21]=[CH:20]1)N>>CC1=C[N:10]2[CH:20]1[CH-:21][C@@H]2N

[H:11][C:4]1=[C:3]([C@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '4\tpi\t3\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@:20](C=C1)N 10=20;20,21=21
n_N > π^*_C=C CC1=C[N-:10][C@H]([CH:21]=[CH:20]1)N>>CC1=C[N:10]2[CH:20]1[CH-:21][C@@H]2N 10=20;20,21=21
87

CC1=C[N-:10][C@H:21](C=C1)[NH2:20]>>CC1=C[N:10]([C@@H-:21]C=C1)[NH2:20]

[H:11][C:4]1=[C:3]([C@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '8\tsigma\t1\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@:20](C=C1)N 10=20;20,21=21
n_N > σ^*_N-C CC1=C[N-:10][C@H:21](C=C1)[NH2:20]>>CC1=C[N:10]([C@@H-:21]C=C1)[NH2:20] 10=20;20,21=21
87

[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '4\tpi\t3\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
n_N > π^*_C=C CC1=C[N-:10][C@@H]([CH:21]=[CH:20]1)N>>CC1=C[N:10]2[CH:20]1[CH-:21][C@H]2N 10=20;20,21=21
90

[H:20][CH2:21][C:22]1=[CH:23][N-:10][C@@H](C=C1)N>>[H:20][N:10]1[CH-:23][C:22](=[CH2:21])C=C[C@H]1N

[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '13\tsigma\t7\t2; 5\tpi\t6\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
n_N > σ^*_H-C > π^*_C=C [H:20][CH2:21][C:22]1=[CH:23][N-:10][C@@H](C=C1)N>>[H:20][N:10]1[CH-:23][C:22](=[CH2:21])C=C[C@H]1N 10=20;20,21=21,22;22,23=23
90

[H:11][C:10]1=C[C@@:20]([N-]C=C1C)([H:21])N>>[H-:21].[H+:11].CC1=C[N-][C@@:20]2([C:10]1=C2)N

[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('4\tsigma\t11\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
σ_C-H > σ^*_C-H [H:11][C:10]1=C[C@@:20]([N-]C=C1C)([H:21])N>>[H-:21].[H+:11].CC1=C[N-][C@@:20]2([C:10]1=C2)N 10,11=10,20;20,21=21
90

[H:21][C@:20]1(C=C[C:11](=[CH:10][N-]1)C)N>>[H-:21].C[C+:11]1C=C[C@:20]2([CH:10]1[N-]2)N

[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('6\tpi\t5\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N>>[H-:21].CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
π_C=C > σ^*_C-H [H:21][C@:20]1(C=C[C:11](=[CH:10][N-]1)C)N>>[H-:21].C[C+:11]1C=C[C@:20]2([CH:10]1[N-]2)N 10,11=10,20;20,21=21
90

[H:21][C@:20]1(C=CC(=C[N-:10]1)C)N.CC1=C[N-][C@@H](C=C1)N>>[H-:21].CC1=C[N-][C@@H](C=C1)N.CC1=C[N:10]=[C@@:20](C=C1)N

[H:21][C@:20]1(C=CC(=C[N-]1)C)N.CC1=C[N-:11][C@@H:10](C=C1)N>>[H-:21].CC1=C[N-][C@@:20](C=C1)([C@H:10](C=CC(=C[N:11])C)N)N

[H:10011][C:10004]1=[C:10003]([C@@:10001]([N-:10002][C:10006](=[C:10005]1[C:10007]([H:10013])([H:10014])[H:10015])[H:10012])([H:10010])[N:10008]([H:10016])[H:10017])[H:10009].[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('10001\tsigma\t10002\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N.CC1=C[N-][C@@H](C=C1)N>>[H-:21].CC1=C[N-][C@@H](C=C1)N.CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
σ_C-N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-]1)C)N.CC1=C[N-:11][C@@H:10](C=C1)N>>[H-:21].CC1=C[N-][C@@:20](C=C1)([C@H:10](C=CC(=C[N:11])C)N)N 10,11=10,20;20,21=21
92

[H:21][C@:20]1(C=CC(=C[N-]1)C)N.CC1=C[N-:13][C@@H:12]([CH:11]=[CH:10]1)N>>[H-:21].CC1=C[N-][C@@:20](C=C1)([CH:10]([CH:11]=[C@@H:12]N)C(=C[N:13])C)N

[H:10011][C:10004]1=[C:10003]([C@@:10001]([N-:10002][C:10006](=[C:10005]1[C:10007]([H:10013])([H:10014])[H:10015])[H:10012])([H:10010])[N:10008]([H:10016])[H:10017])[H:10009].[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('10004\tpi\t10003\t2; 10001\tsigma\t10002\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N.CC1=C[N-][C@@H](C=C1)N>>[H-:21].CC1=C[N-][C@@H](C=C1)N.CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
σ_C-N > π_C=C > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-]1)C)N.CC1=C[N-:13][C@@H:12]([CH:11]=[CH:10]1)N>>[H-:21].CC1=C[N-][C@@:20](C=C1)([CH:10]([CH:11]=[C@@H:12]N)C(=C[N:13])C)N 10,11=10,20;12,13=11,12;20,21=21
92

[H:11][C@:10]1(C=CC(=C[N-]1)C)N.[H:21][C@:20]1(C=CC(=C[N-]1)C)N>>[H-:21].[H+:11].CC1=C[N-][C@:10](C=C1)([C@@:20]2(C=CC(=C[N-]2)C)N)N

[H:10011][C:10004]1=[C:10003]([C@@:10001]([N-:10002][C:10006](=[C:10005]1[C:10007]([H:10013])([H:10014])[H:10015])[H:10012])([H:10010])[N:10008]([H:10016])[H:10017])[H:10009].[H:11][C:4]1=[C:3]([C@@:1]([N-:2][C:6](=[C:5]1[C:7]([H:13])([H:14])[H:15])[H:12])([H:10])[N:8]([H:16])[H:17])[H:9]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('10001\tsigma\t10010\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C=CC(=C[N-:10]1)C)N.CC1=C[N-][C@@H](C=C1)N>>[H-:21].CC1=C[N-][C@@H](C=C1)N.CC1=C[N:10]=[C@@:20](C=C1)N 10=20;20,21=21
σ_C-H > σ^*_C-H [H:11][C@:10]1(C=CC(=C[N-]1)C)N.[H:21][C@:20]1(C=CC(=C[N-]1)C)N>>[H-:21].[H+:11].CC1=C[N-][C@:10](C=C1)([C@@:20]2(C=CC(=C[N-]2)C)N)N 10,11=10,20;20,21=21
92

[H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N

CC1=CC=C[N-:10][C@H:20]1[NH2:21]>>CC1=CC=C[N:10]=[C@@H:20]1.[NH2-:21]

[H:11][C:5]1=[C:6]([N-:2][C@@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '1\tsigma\t8\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N 10=20;20,21=21
n_N > σ^*_C-N CC1=CC=C[N-:10][C@H:20]1[NH2:21]>>CC1=CC=C[N:10]=[C@@H:20]1.[NH2-:21] 10=20;20,21=21
93

CC1=[CH:20][CH:21]=C[N-:10][C@H]1N>>CC1=[CH:20][N:10]([C@H]1N)C=[CH-:21]

[H:11][C:5]1=[C:6]([N-:2][C@@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '4\tsigma\t5\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N 10=20;20,21=21
n_N > σ^*_C-C CC1=[CH:20][CH:21]=C[N-:10][C@H]1N>>CC1=[CH:20][N:10]([C@H]1N)C=[CH-:21] 10=20;20,21=21
93

[H:21][C:20]1=C[N-:10][C@H](C(=C1)C)N>>[H-:21].CC1=C[C:20]2=C[N:10]2[C@H]1N

[H:11][C:5]1=[C:6]([N-:2][C@@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '5\tsigma\t11\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N 10=20;20,21=21
n_N > σ^*_C-H [H:21][C:20]1=C[N-:10][C@H](C(=C1)C)N>>[H-:21].CC1=C[C:20]2=C[N:10]2[C@H]1N 10=20;20,21=21
93

[H:13][C:12]1=C[N-][C@@:20]([C:10](=[CH:11]1)C)([H:21])N>>[H-:21].[H+:13].C[C:10]1=[C@@:20]([N-]C=[C:12]=[CH:11]1)N

[H:11][C:5]1=[C:6]([N-:2][C@@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('3\tpi\t4\t2; 5\tsigma\t11\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N 10=20;20,21=21
σ_C-H > π_C=C > σ^*_C-H [H:13][C:12]1=C[N-][C@@:20]([C:10](=[CH:11]1)C)([H:21])N>>[H-:21].[H+:13].C[C:10]1=[C@@:20]([N-]C=[C:12]=[CH:11]1)N 10,11=10,20;12,13=11,12;20,21=21
93

[H:11][C:10]1=CC=C([C@:20]([N-]1)([H:21])N)C>>[H-:21].[H+:11].CC1=CC=[C:10]2[C@@:20]1([N-]2)N

[H:11][C:5]1=[C:6]([N-:2][C@@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('6\tsigma\t12\t2', '1\tsigma\t10\t2')
n_N > σ^*_C-H [H:21][C@@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@:20]1N 10=20;20,21=21
σ_C-H > σ^*_C-H [H:11][C:10]1=CC=C([C@:20]([N-]1)([H:21])N)C>>[H-:21].[H+:11].CC1=CC=[C:10]2[C@@:20]1([N-]2)N 10,11=10,20;20,21=21
93

[H:20][C@:21]1([C:22](=[CH:23]C=C[N-:10]1)C)N>>[H:20][N:10]1C=C[CH-:23][C:22](=[C@:21]1N)C

[H:11][C:5]1=[C:6]([N-:2][C@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '10\tsigma\t1\t2; 3\tpi\t4\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@@:20]1N 10=20;20,21=21
n_N > σ^*_H-C > π^*_C=C [H:20][C@:21]1([C:22](=[CH:23]C=C[N-:10]1)C)N>>[H:20][N:10]1C=C[CH-:23][C:22](=[C@:21]1N)C 10=20;20,21=21,22;22,23=23
96

[H:21][CH2:20]C1=CC=C[N-:10][C@@H]1N>>[H-:21].[CH2:20]1C2=CC=C[N:10]1[C@@H]2N

[H:11][C:5]1=[C:6]([N-:2][C@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '7\tsigma\t13\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@@:20]1N 10=20;20,21=21
n_N > σ^*_C-H [H:21][CH2:20]C1=CC=C[N-:10][C@@H]1N>>[H-:21].[CH2:20]1C2=CC=C[N:10]1[C@@H]2N 10=20;20,21=21
96

[H:20][C:21]1=CC=C([C@H]([N-:10]1)N)C>>[H:20][N:10]1[C-:21]=CC=C([C@H]1N)C

[H:11][C:5]1=[C:6]([N-:2][C@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '12\tsigma\t6\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C(=CC=C[N-:10]1)C)N>>[H-:21].CC1=CC=C[N:10]=[C@@:20]1N 10=20;20,21=21
n_N > σ^*_H-C [H:20][C:21]1=CC=C([C@H]([N-:10]1)N)C>>[H:20][N:10]1[C-:21]=CC=C([C@H]1N)C 10=20;20,21=21
96

[H:21][C@:20]1(C(=CC=C[N-:10]1)C)N.CC1=CC=C[N-][C@@H]1N>>[H-:21].CC1=CC=C[N-][C@@H]1N.CC1=CC=C[N:10]=[C@@:20]1N

CC1=C[CH:20]=[CH:21][N-:22][C@@H:23]1N.CC1=CC=C[N-:10][C@@H]1N>>CC1=CC=C[N:10]([C@@H]1N)[CH:20](C=C(C)[C@H-:23]N)[CH:21]=[N-:22]

[H:10011][C:10005]1=[C:10006]([N-:10002][C@:10001]([C:10003](=[C:10004]1[H:10009])[C:10007]([H:10013])([H:10014])[H:10015])([H:10010])[N:10008]([H:10016])[H:10017])[H:10012].[H:11][C:5]1=[C:6]([N-:2][C@:1]([C:3](=[C:4]1[H:9])[C:7]([H:13])([H:14])[H:15])([H:10])[N:8]([H:16])[H:17])[H:12]
('2\tsp3\tNone\t2', '1\tsigma\t10\t2') ('2\tsp3\tNone\t2', '10005\tpi\t10006\t2; 10002\tsigma\t10001\t2')
n_N > σ^*_C-H [H:21][C@:20]1(C(=CC=C[N-:10]1)C)N.CC1=CC=C[N-][C@@H]1N>>[H-:21].CC1=CC=C[N-][C@@H]1N.CC1=CC=C[N:10]=[C@@:20]1N 10=20;20,21=21
n_N > π^*_C=C > σ^*_N-C CC1=C[CH:20]=[CH:21][N-:22][C@@H:23]1N.CC1=CC=C[N-:10][C@@H]1N>>CC1=CC=C[N:10]([C@@H]1N)[CH:20](C=C(C)[C@H-:23]N)[CH:21]=[N-:22] 10=20;20,21=21,22;22,23=23
97

[H:20][CH2:21]c1ccncc1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccncc1

Cc1[cH:21][cH:20]ncc1.[NH2-:10]>>[cH-:21]=c(C)c=cn=[cH:20][NH2:10]

[H:12][c:2]1[c:6]([n:7][c:8]([c:9]([c:1]1[C:3]([H:4])([H:10])[H:11])[H:15])[H:14])[H:13].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '6\tpi\t2\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccncc1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccncc1 10=20;20,21=21
n_N > π^*_C-C Cc1[cH:21][cH:20]ncc1.[NH2-:10]>>[cH-:21]=c(C)c=cn=[cH:20][NH2:10] 10=20;20,21=21
99

[H:20][c:21]1[cH:22][c:23](ccn1)C.[NH2-:10]>>[H:20][NH2:10].[cH:22]=[c:21]n=cc=[c-:23]C

[H:12][c:2]1[c:6]([n:7][c:8]([c:9]([c:1]1[C:3]([H:4])([H:10])[H:11])[H:15])[H:14])[H:13].[H:16][N-:5][H:17]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '14\tsigma\t8\t2; 9\tpi\t1\t2')
n_N > σ^*_H-C [H:20][CH2:21]c1ccncc1.[NH2-:10]>>[H:20][NH2:10].[CH2-:21]c1ccncc1 10=20;20,21=21
n_N > σ^*_H-C > π^*_C-C [H:20][c:21]1[cH:22][c:23](ccn1)C.[NH2-:10]>>[H:20][NH2:10].[cH:22]=[c:21]n=cc=[c-:23]C 10=20;20,21=21,22;22,23=23
99

[H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-:10]>>[H:20][NH2:10].C[C:21]1=[C:22](CCC1=O)[O-:23]

[H:20][CH:21]1[CH:22](C(=O)C(C1=O)C)[H:23].[NH2-:10]>>[H-:23].[H:20][NH2:10].CC1C(=O)[CH:21]=[CH:22]C1=O

[H:13][C:9]1([C:1](=[O:2])[C:3]([C:6](=[O:7])[C:8]1([H:11])[H:12])([H:4])[C:10]([H:15])([H:16])[H:17])[H:14].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '13\tsigma\t9\t2; 8\tsigma\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-:10]>>[H:20][NH2:10].C[C:21]1=[C:22](CCC1=O)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-H [H:20][CH:21]1[CH:22](C(=O)C(C1=O)C)[H:23].[NH2-:10]>>[H-:23].[H:20][NH2:10].CC1C(=O)[CH:21]=[CH:22]C1=O 10=20;20,21=21,22;22,23=23
102

[H:20][C:21]1([C:22](=[O:23])CC[C:10]1=[O:11])C.[NH2-]>>[H:20][C:10]1(CC[C:22](=[C:21]1C)[O-:23])[O+:11].[NH2-]

[H:13][C:9]1([C:1](=[O:2])[C:3]([C:6](=[O:7])[C:8]1([H:11])[H:12])([H:4])[C:10]([H:15])([H:16])[H:17])[H:14].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('6\tpi\t7\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-:10]>>[H:20][NH2:10].C[C:21]1=[C:22](CCC1=O)[O-:23] 10=20;20,21=21,22;22,23=23
π_C=O > σ^*_H-C > π^*_C=O [H:20][C:21]1([C:22](=[O:23])CC[C:10]1=[O:11])C.[NH2-]>>[H:20][C:10]1(CC[C:22](=[C:21]1C)[O-:23])[O+:11].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
102

[H:10][CH:11]1CC(=O)[C:21]([C:22]1=[O:23])([H:20])C.[NH2-]>>[H:10][H:20].C[C:21]1=[C:22]([CH+:11]CC1=O)[O-:23].[NH2-]

[H:13][C:9]1([C:1](=[O:2])[C:3]([C:6](=[O:7])[C:8]1([H:11])[H:12])([H:4])[C:10]([H:15])([H:16])[H:17])[H:14].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('13\tsigma\t9\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-:10]>>[H:20][NH2:10].C[C:21]1=[C:22](CCC1=O)[O-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > π^*_C=O [H:10][CH:11]1CC(=O)[C:21]([C:22]1=[O:23])([H:20])C.[NH2-]>>[H:10][H:20].C[C:21]1=[C:22]([CH+:11]CC1=O)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
102

[H:20][C:21]1([C:22](=[O:23])CCC1=O)C.CC1C(=O)CCC1=O.[NH2-:10]>>[H:20][NH2:10].CC1C(=O)CCC1=O.C[C:21]1=[C:22](CCC1=O)[O-:23]

[H:11][C:10]1(C(=O)CCC1=O)C.[H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-]>>[H+:11].[H:20][C:10]1(C(=O)CCC1=O)C.C[C:21]1=[C:22](CCC1=O)[O-:23].[NH2-]

[H:10013][C:10009]1([C:10001](=[O:10002])[C:10003]([C:10006](=[O:10007])[C:10008]1([H:10011])[H:10012])([H:10004])[C:10010]([H:10015])([H:10016])[H:10017])[H:10014].[H:13][C:9]1([C:1](=[O:2])[C:3]([C:6](=[O:7])[C:8]1([H:11])[H:12])([H:4])[C:10]([H:15])([H:16])[H:17])[H:14].[H:18][N-:5][H:19]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10003\tsigma\t10004\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][C:21]1([C:22](=[O:23])CCC1=O)C.CC1C(=O)CCC1=O.[NH2-:10]>>[H:20][NH2:10].CC1C(=O)CCC1=O.C[C:21]1=[C:22](CCC1=O)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-H > σ^*_H-C > π^*_C=O [H:11][C:10]1(C(=O)CCC1=O)C.[H:20][C:21]1([C:22](=[O:23])CCC1=O)C.[NH2-]>>[H+:11].[H:20][C:10]1(C(=O)CCC1=O)C.C[C:21]1=[C:22](CCC1=O)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
104

[H:20][CH2:21][C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].[CH2:21]=[C:22]([O-:23])Cl

[CH3:21][C:20](=O)Cl.[NH2-:10]>>[CH3-:21].[C:20](=O)([NH2:10])Cl

[H:4][C:3]([H:7])([H:8])[C:1](=[O:2])[Cl:6].[H:9][N-:5][H:10]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '1\tsigma\t3\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH2:21][C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].[CH2:21]=[C:22]([O-:23])Cl 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-C [CH3:21][C:20](=O)Cl.[NH2-:10]>>[CH3-:21].[C:20](=O)([NH2:10])Cl 10=20;20,21=21
105

C=C([O-])Cl.C=[C:20]([O-:10])[Cl:21]>>C=[C:20]=[O:10].C=C([O-])Cl.[Cl-:21]

C=[C:10]([O-])[Cl:11].C=[C:20]([O-])[Cl:21]>>C=[C:10]([C:20](=C)[O-])[O-].[Cl-:21].[Cl+:11]

[H:10005][C:10004](=[C:10001]([O-:10002])[Cl:10003])[H:10006].[H:5][C:4](=[C:1]([O-:2])[Cl:3])[H:6]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('10001\tsigma\t10003\t2', '1\tsigma\t3\t2')
n_O > σ^*_C-Cl C=C([O-])Cl.C=[C:20]([O-:10])[Cl:21]>>C=[C:20]=[O:10].C=C([O-])Cl.[Cl-:21] 10=20;20,21=21
σ_C-Cl > σ^*_C-Cl C=[C:10]([O-])[Cl:11].C=[C:20]([O-])[Cl:21]>>C=[C:10]([C:20](=C)[O-])[O-].[Cl-:21].[Cl+:11] 10,11=10,20;20,21=21
110

[H:10][CH2:11][CH:21]([H:20])[N+](=O)[O-].[NH2-]>>[H:10][H:20].[CH2+:11][CH-:21][N+](=O)[O-].[NH2-]

[H:9][C:1]([H:10])([H:11])[C:3]([H:4])([H:8])[N+:2](=[O:6])[O-:7].[H:12][N-:5][H:13]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('9\tsigma\t1\t2', '4\tsigma\t3\t2')
n_N > σ^*_H-C [H:20][CH:21](C)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].C[CH-:21][N+](=O)[O-] 10=20;20,21=21
σ_H-C > σ^*_H-C [H:10][CH2:11][CH:21]([H:20])[N+](=O)[O-].[NH2-]>>[H:10][H:20].[CH2+:11][CH-:21][N+](=O)[O-].[NH2-] 10,11=10,20;20,21=21
114

[H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23]

C[C:23](=O)[CH2:22][C:21](=[O:20])Cc1ccccc1.[NH2-:10]>>C[C-:23]=O.[CH2:22]=[C:21](Cc1ccccc1)[O:20][NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '7\tpi\t6\t2; 3\tsigma\t1\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_O=C > σ^*_C-C C[C:23](=O)[CH2:22][C:21](=[O:20])Cc1ccccc1.[NH2-:10]>>C[C-:23]=O.[CH2:22]=[C:21](Cc1ccccc1)[O:20][NH2:10] 10=20;20,21=21,22;22,23=23
117

CC(=O)CC(=O)C[c:21]1cccc[cH:20]1.[NH2-:10]>>CC(=O)CC(=O)C[c-:21]1cccc[cH:20]1[NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '10\tsigma\t9\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C CC(=O)CC(=O)C[c:21]1cccc[cH:20]1.[NH2-:10]>>CC(=O)CC(=O)C[c-:21]1cccc[cH:20]1[NH2:10] 10=20;20,21=21
117

CC(=O)CC(=O)Cc1ccc[cH:21][cH:20]1.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])CC(=O)CC(=O)C

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '10\tpi\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C CC(=O)CC(=O)Cc1ccc[cH:21][cH:20]1.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])CC(=O)CC(=O)C 10=20;20,21=21
117

C[C:21](=[O:20])CC(=O)Cc1ccccc1.[NH2-:10]>>C[C-:21](CC(=O)Cc1ccccc1)[O:20][NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '2\tpi\t1\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_O=C C[C:21](=[O:20])CC(=O)Cc1ccccc1.[NH2-:10]>>C[C-:21](CC(=O)Cc1ccccc1)[O:20][NH2:10] 10=20;20,21=21
117

[H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.CC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccccc1.C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23]

[H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.C[C:11](=O)[CH2:10]C(=O)Cc1ccccc1.[NH2-]>>[H:20][CH2:10]C(=O)Cc1ccccc1.C[C+:11]=O.C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-]

[H:10021][c:10012]1[c:10013]([c:10014]([c:10009]([c:10010]([c:10011]1[H:10020])[H:10019])[C:10008]([H:10017])([H:10018])[C:10006](=[O:10007])[C:10003]([H:10004])([H:10016])[C:10001](=[O:10002])[C:10015]([H:10024])([H:10025])[H:10026])[H:10023])[H:10022].[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10003\tsigma\t10001\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.CC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccccc1.C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.C[C:11](=O)[CH2:10]C(=O)Cc1ccccc1.[NH2-]>>[H:20][CH2:10]C(=O)Cc1ccccc1.C[C+:11]=O.C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
119

[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.CC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccccc1.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23]

[H:13][CH:12]([C:11](=[O:10])C)C(=O)Cc1ccccc1.[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[NH2-]>>[H+:13].[H:20][O:10][C:11](=[CH:12]C(=O)Cc1ccccc1)C.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-]

[H:10024][c:10013]1[c:10014]([c:10015]([c:10010]([c:10011]([c:10012]1[H:10023])[H:10022])[C:10009]([H:10020])([H:10021])[C:10001](=[O:10002])[C:10003]([H:10004])([H:10016])[C:10006](=[O:10007])[C:10008]([H:10017])([H:10018])[H:10019])[H:10026])[H:10025].[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10007\tpi\t10006\t2; 10003\tsigma\t10004\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.CC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccccc1.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-H > π_O=C > σ^*_H-C > π^*_C=O [H:13][CH:12]([C:11](=[O:10])C)C(=O)Cc1ccccc1.[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[NH2-]>>[H+:13].[H:20][O:10][C:11](=[CH:12]C(=O)Cc1ccccc1)C.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
121

[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.C[C:13](=O)[CH2:12][C:11](=[O:10])Cc1ccccc1.[NH2-]>>[H:20][O:10][C:11](=[CH2:12])Cc1ccccc1.C[C+:13]=O.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-]

[H:10024][c:10013]1[c:10014]([c:10015]([c:10010]([c:10011]([c:10012]1[H:10023])[H:10022])[C:10009]([H:10020])([H:10021])[C:10001](=[O:10002])[C:10003]([H:10004])([H:10016])[C:10006](=[O:10007])[C:10008]([H:10017])([H:10018])[H:10019])[H:10026])[H:10025].[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10002\tpi\t10001\t2; 10003\tsigma\t10006\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.CC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccccc1.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-C > π_O=C > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.C[C:13](=O)[CH2:12][C:11](=[O:10])Cc1ccccc1.[NH2-]>>[H:20][O:10][C:11](=[CH2:12])Cc1ccccc1.C[C+:13]=O.CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
121

[H:20][CH:21]([c:22]1cccc[cH:23]1)C(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)[CH:21]=[c:22]1[cH-:23]cccc1

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '17\tsigma\t8\t2; 9\tsigma\t10\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C:C [H:20][CH:21]([c:22]1cccc[cH:23]1)C(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)[CH:21]=[c:22]1[cH-:23]cccc1 10=20;20,21=21,22;22,23=23
122

CC(=O)CC(=O)Cc1cc[cH:21][cH:20]c1.[NH2-:10]>>CC(=O)CC(=O)Cc1cc[cH-:21][cH:20](c1)[NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '11\tsigma\t12\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C CC(=O)CC(=O)Cc1cc[cH:21][cH:20]c1.[NH2-:10]>>CC(=O)CC(=O)Cc1cc[cH-:21][cH:20](c1)[NH2:10] 10=20;20,21=21
122

[H:21][c:20]1cccc(c1)CC(=O)CC(=O)C.[NH2-:10]>>[H-:21].CC(=O)CC(=O)Cc1ccc[c:20](c1)[NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '11\tsigma\t20\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-H [H:21][c:20]1cccc(c1)CC(=O)CC(=O)C.[NH2-:10]>>[H-:21].CC(=O)CC(=O)Cc1ccc[c:20](c1)[NH2:10] 10=20;20,21=21
122

[H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=c([c:21]=[cH:22])CC(=O)CC(=O)C

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '23\tsigma\t14\t2; 13\tpi\t12\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > π^*_C-C [H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=c([c:21]=[cH:22])CC(=O)CC(=O)C 10=20;20,21=21,22;22,23=23
122

CC(=O)CC(=O)Cc1[cH:20][cH:21]ccc1.[NH2-:10]>>CC(=O)CC(=O)Cc1ccc[cH-:21][cH:20]1[NH2:10]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '14\tsigma\t13\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C CC(=O)CC(=O)Cc1[cH:20][cH:21]ccc1.[NH2-:10]>>CC(=O)CC(=O)Cc1ccc[cH-:21][cH:20]1[NH2:10] 10=20;20,21=21
122

[H:20][c:21]1cccc(c1)CC(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccc[c-:21]c1

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[C:15]([H:24])([H:25])[H:26])[H:23])[H:22].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '20\tsigma\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C)C(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].C[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C [H:20][c:21]1cccc(c1)CC(=O)CC(=O)C.[NH2-:10]>>[H:20][NH2:10].CC(=O)CC(=O)Cc1ccc[c-:21]c1 10=20;20,21=21
122

[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23]

[H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[H:10][NH-:11]>>[H:20][H:10].CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH:11]

[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('27\tsigma\t5\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_H-N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C)[C:22](=[O:23])Cc1ccccc1.[H:10][NH-:11]>>[H:20][H:10].CC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH:11] 10,11=10,20;20,21=21,22;22,23=23
125

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23]

[H:20][CH:21](c1ccccc1)[C:22](=O)[CH2:23]C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[CH2-:23]C(=O)Cl.c1ccc(cc1)[CH:21]=[C:22]=O

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '17\tsigma\t9\t2; 1\tsigma\t3\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C-C [H:20][CH:21](c1ccccc1)[C:22](=O)[CH2:23]C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[CH2-:23]C(=O)Cl.c1ccc(cc1)[CH:21]=[C:22]=O 10=20;20,21=21,22;22,23=23
127

c1c[cH:20][c:21](cc1)[CH2:22][C:23](=O)CC(=O)Cl.[NH2-:10]>>[CH2:22]=[c:21]=cc=cc=[cH:20][NH2:10].C([C-:23]=O)C(=O)Cl

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '15\tpi\t10\t2; 9\tsigma\t1\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > σ^*_C-C c1c[cH:20][c:21](cc1)[CH2:22][C:23](=O)CC(=O)Cl.[NH2-:10]>>[CH2:22]=[c:21]=cc=cc=[cH:20][NH2:10].C([C-:23]=O)C(=O)Cl 10=20;20,21=21,22;22,23=23
127

[H:23][CH:22]([c:21]1[cH:20]cccc1)C(=O)CC(=O)Cl.[NH2-:10]>>[H-:23].c(=cc=[c:21]=[CH:22]C(=O)CC(=O)Cl)c=[cH:20][NH2:10]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '15\tpi\t10\t2; 9\tsigma\t17\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > σ^*_C-H [H:23][CH:22]([c:21]1[cH:20]cccc1)C(=O)CC(=O)Cl.[NH2-:10]>>[H-:23].c(=cc=[c:21]=[CH:22]C(=O)CC(=O)Cl)c=[cH:20][NH2:10] 10=20;20,21=21,22;22,23=23
127

[H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[cH-:23]1[cH]cc([c:21][cH:22]1)CC(=O)CC(=O)Cl

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '19\tsigma\t11\t2; 12\tsigma\t13\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C:C [H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[cH-:23]1[cH]cc([c:21][cH:22]1)CC(=O)CC(=O)Cl 10=20;20,21=21,22;22,23=23
127

[H:21][c:20]1cccc(c1)CC(=O)CC(=O)Cl.[NH2-:10]>>[H-:21].c1cc(c[c:20](c1)[NH2:10])CC(=O)CC(=O)Cl

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '12\tsigma\t20\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-H [H:21][c:20]1cccc(c1)CC(=O)CC(=O)Cl.[NH2-:10]>>[H-:21].c1cc(c[c:20](c1)[NH2:10])CC(=O)CC(=O)Cl 10=20;20,21=21
127

[H:21][c:20]1ccc(cc1)CC(=O)CC(=O)Cl.[NH2-:10]>>[H-:21].c1c[c:20](ccc1CC(=O)CC(=O)Cl)[NH2:10]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '13\tsigma\t21\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-H [H:21][c:20]1ccc(cc1)CC(=O)CC(=O)Cl.[NH2-:10]>>[H-:21].c1c[c:20](ccc1CC(=O)CC(=O)Cl)[NH2:10] 10=20;20,21=21
127

[H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=c([c:21]=[cH:22])CC(=O)CC(=O)Cl

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '23\tsigma\t15\t2; 14\tpi\t13\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > π^*_C-C [H:20][c:21]1[cH:22][cH:23]ccc1CC(=O)CC(=O)Cl.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=c([c:21]=[cH:22])CC(=O)CC(=O)Cl 10=20;20,21=21,22;22,23=23
127

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:10](=[O:11])Cl.[NH2-]>>[H:20][C:10]([CH:21]=[C:22](Cc1ccccc1)[O-:23])([O+:11])Cl.[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('6\tpi\t7\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
π_C=O > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:10](=[O:11])Cl.[NH2-]>>[H:20][C:10]([CH:21]=[C:22](Cc1ccccc1)[O-:23])([O+:11])Cl.[NH2-] 10,11=10,20;20,21=21,22;22,23=23
127

[H:20][CH:21]([C:22](=[O:23])[CH2:11][c:10]1ccccc1)C(=O)Cl.[NH2-]>>[H:20][c:10]1ccccc1.[CH2+:11][C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10\tsigma\t9\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])[CH2:11][c:10]1ccccc1)C(=O)Cl.[NH2-]>>[H:20][c:10]1ccccc1.[CH2+:11][C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
127

[H:20][CH:21]([C:22](=[O:23])Cc1[cH:10][cH:11]ccc1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1[cH+:11]cccc1C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('15\tsigma\t14\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1[cH:10][cH:11]ccc1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1[cH+:11]cccc1C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
127

[H:10][CH:11](c1ccccc1)[C:22](=[O:23])[CH:21]([H:20])C(=O)Cl.[NH2-]>>[H:10][H:20].c1ccc(cc1)[CH+:11][C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('17\tsigma\t9\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > π^*_C=O [H:10][CH:11](c1ccccc1)[C:22](=[O:23])[CH:21]([H:20])C(=O)Cl.[NH2-]>>[H:10][H:20].c1ccc(cc1)[CH+:11][C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
127

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)[CH:21]=[C:22]([O-:23])Cl

[H:20][CH:21](C(=O)[CH2:11][c:10]1ccccc1)[C:22](=[O:23])Cl.[NH2-]>>[H:20][c:10]1ccccc1.[CH2+:11]C(=O)[CH:21]=[C:22]([O-:23])Cl.[NH2-]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[Cl:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('9\tsigma\t8\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)[CH:21]=[C:22]([O-:23])Cl 10=20;20,21=21,22;22,23=23
σ_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)[CH2:11][c:10]1ccccc1)[C:22](=[O:23])Cl.[NH2-]>>[H:20][c:10]1ccccc1.[CH2+:11]C(=O)[CH:21]=[C:22]([O-:23])Cl.[NH2-] 10,11=10,20;20,21=21,22;22,23=23
130

[cH:21]1[cH:20]cc(cc1)CC(=O)CC(=O)Cl.[NH2-:10]>>[cH-:21]=cc=c(c=[cH:20][NH2:10])CC(=O)CC(=O)Cl

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '14\tpi\t13\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C [cH:21]1[cH:20]cc(cc1)CC(=O)CC(=O)Cl.[NH2-:10]>>[cH-:21]=cc=c(c=[cH:20][NH2:10])CC(=O)CC(=O)Cl 10=20;20,21=21
132

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:11](=[O:10])[Cl:12].[NH2-]>>[H:20][O:10][C:11](=[Cl+:12])[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('7\tpi\t6\t2; 8\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
n_Cl > π_O=C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:11](=[O:10])[Cl:12].[NH2-]>>[H:20][O:10][C:11](=[Cl+:12])[CH:21]=[C:22](Cc1ccccc1)[O-:23].[NH2-] 10,11=10,20;12=11;20,21=21,22;22,23=23
132

[H:11][CH:10](c1ccccc1)[C:22](=[O:23])[CH:21]([H:20])C(=O)Cl.[NH2-]>>[H+:11].[H:20][CH:10](c1ccccc1)[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('9\tsigma\t17\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-H > σ^*_H-C > π^*_C=O [H:11][CH:10](c1ccccc1)[C:22](=[O:23])[CH:21]([H:20])C(=O)Cl.[NH2-]>>[H+:11].[H:20][CH:10](c1ccccc1)[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
132

[H:20][CH:21]([C:22](=[O:23])C[c:10]1cccc[cH:11]1)C(=O)Cl.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10\tsigma\t11\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C[c:10]1cccc[cH:11]1)C(=O)Cl.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
132

[H:20][CH:21]([C:22](=[O:23])C[c:11]1cccc[cH:10]1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1cccc[c+:11]1C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('11\tsigma\t10\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])C[c:11]1cccc[cH:10]1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1cccc[c+:11]1C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
132

[H:20][CH:21]([C:22](=[O:23])Cc1cc[cH:10][cH:11]c1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1ccc(c[cH+:11]1)C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('13\tsigma\t12\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1cc[cH:10][cH:11]c1)C(=O)Cl.[NH2-]>>[H:20][cH:10]1ccc(c[cH+:11]1)C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
132

[H:20][CH:21]([C:22](=[O:23])Cc1c[cH:10][cH:11]cc1)C(=O)Cl.[NH2-]>>[H:20][cH:10]=cc(=cc=[cH+:11])C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-]

[H:21][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:20])[H:19])[C:9]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[C:6](=[O:7])[Cl:8])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('14\tpi\t13\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C(=O)Cl)[O-:23] 10=20;20,21=21,22;22,23=23
π_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1c[cH:10][cH:11]cc1)C(=O)Cl.[NH2-]>>[H:20][cH:10]=cc(=cc=[cH+:11])C[C:22](=[CH:21]C(=O)Cl)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
132

[H:20][CH:21]([C:10](=[O:11])Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-]>>[H:20][C:10](Cc1ccccc1)([CH:21]=[C:22]([O-:23])Cl)[O+:11].[NH2-]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[Cl:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('6\tpi\t7\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)[CH:21]=[C:22]([O-:23])Cl 10=20;20,21=21,22;22,23=23
π_C=O > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:10](=[O:11])Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-]>>[H:20][C:10](Cc1ccccc1)([CH:21]=[C:22]([O-:23])Cl)[O+:11].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
135

[H:13][c:12]1ccc[cH:10][c:11]1CC(=O)[CH:21]([H:20])[C:22](=[O:23])Cl.[NH2-]>>[H+:13].[H:20][cH:10]=cc=c[c:12]=[c:11]CC(=O)[CH:21]=[C:22]([O-:23])Cl.[NH2-]

[H:21][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:20])[H:19])[C:8]([H:17])([H:18])[C:6](=[O:7])[C:3]([H:4])([H:16])[C:1](=[O:2])[Cl:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('14\tpi\t9\t2; 10\tsigma\t19\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])Cl.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)[CH:21]=[C:22]([O-:23])Cl 10=20;20,21=21,22;22,23=23
σ_C-H > π_C-C > σ^*_H-C > π^*_C=O [H:13][c:12]1ccc[cH:10][c:11]1CC(=O)[CH:21]([H:20])[C:22](=[O:23])Cl.[NH2-]>>[H+:13].[H:20][cH:10]=cc=c[c:12]=[c:11]CC(=O)[CH:21]=[C:22]([O-:23])Cl.[NH2-] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
135

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $[cH:21]1ccc(c[cH:20]1)CC(=O)/C=C(\[O-:10])/Cl>>[cH-:21]1ccc2c[cH:20]1[O:10]/C(=C\C(=O)C2)/Cl$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('2\tsp3\tNone\t2', '5\tsigma\t4\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
n_O > σ^*_C:C [cH:21]1ccc(c[cH:20]1)CC(=O)/C=C(\[O-:10])/Cl>>[cH-:21]1ccc2c[cH:20]1[O:10]/C(=C\C(=O)C2)/Cl 10=20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $c1cc[c:21]([cH:20]c1)CC(=O)/C=C(\[O-:10])/Cl>>c1cc[c-:21]2[cH:20](c1)[O:10]C(=CC(=O)C2)Cl$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('2\tsp3\tNone\t2', '6\tsigma\t7\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
n_O > σ^*_C:C c1cc[c:21]([cH:20]c1)CC(=O)/C=C(\[O-:10])/Cl>>c1cc[c-:21]2[cH:20](c1)[O:10]C(=CC(=O)C2)Cl 10=20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $[cH:21]1[cH:20]cc(cc1)CC(=O)/C=C(\[O-:10])/Cl>>[cH-:21]=cc=c1c[cH:20][O:10]/C(=C\C(=O)C1)/Cl$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('2\tsp3\tNone\t2', '9\tpi\t4\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
n_O > π^*_C-C [cH:21]1[cH:20]cc(cc1)CC(=O)/C=C(\[O-:10])/Cl>>[cH-:21]=cc=c1c[cH:20][O:10]/C(=C\C(=O)C1)/Cl 10=20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $[H:21][CH:20](c1ccccc1)C(=O)/C=C(\[O-:10])/Cl>>[H-:21].c1ccc(cc1)[CH:20]2C(=O)C=C([O:10]2)Cl$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('2\tsp3\tNone\t2', '10\tsigma\t19\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
n_O > σ^*_C-H [H:21][CH:20](c1ccccc1)C(=O)/C=C(\[O-:10])/Cl>>[H-:21].c1ccc(cc1)[CH:20]2C(=O)C=C([O:10]2)Cl 10=20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $c1ccc(cc1)[CH2:21][C:20](=O)/C=C(\[O-:10])/Cl>>[CH2-:21]c1ccccc1.C1=C([O:10][C:20]1=O)Cl$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('2\tsp3\tNone\t2', '11\tsigma\t10\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
n_O > σ^*_C-C c1ccc(cc1)[CH2:21][C:20](=O)/C=C(\[O-:10])/Cl>>[CH2-:21]c1ccccc1.C1=C([O:10][C:20]1=O)Cl 10=20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $c1cc[c:10](cc1)[CH2:11]C(=O)/C=[C:20](\[O-])/[Cl:21]>>[CH2+:11]C(=O)/C=[C:20](/[c:10]1ccccc1)\[O-].[Cl-:21]$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('7\tsigma\t10\t2', '1\tsigma\t3\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
σ_C-C > σ^*_C-Cl c1cc[c:10](cc1)[CH2:11]C(=O)/C=[C:20](\[O-])/[Cl:21]>>[CH2+:11]C(=O)/C=[C:20](/[c:10]1ccccc1)\[O-].[Cl-:21] 10,11=10,20;20,21=21
137

$c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21]$ $[H:13]/[C:12](=[C:20](/[O-])\[Cl:21])/[C:11](=[O:10])Cc1ccccc1>>[H+:13].c1ccc(cc1)C[C:11]2=[C:12]=[C:20]([O:10]2)[O-].[Cl-:21]$
[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('12\tpi\t11\t2; 13\tsigma\t21\t2', '1\tsigma\t3\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].[Cl-:21] 10=20;20,21=21
σ_C-H > π_O=C > σ^*_C-Cl [H:13]/[C:12](=[C:20](/[O-])\[Cl:21])/[C:11](=[O:10])Cc1ccccc1>>[H+:13].c1ccc(cc1)C[C:11]2=[C:12]=[C:20]([O:10]2)[O-].[Cl-:21] 10,11=10,20;12,13=11,12;20,21=21
137

$c1ccc(cc1)CC(=O)/C=C(\[O-])/Cl.c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].c1ccc(cc1)CC(=O)/C=C(\[O-])/Cl.[Cl-:21]$ $c1ccc(cc1)CC(=O)/[CH:11]=[C:10](\[O-])/Cl.c1ccc(cc1)CC(=O)/C=[C:20](\[O-])/[Cl:21]>>c1ccc(cc1)CC(=O)/C=[C:20](/[C:10]([CH+:11]C(=O)Cc2ccccc2)([O-])Cl)\[O-].[Cl-:21]$
[H:10014][c:10004]1[c:10009]([c:10008]([c:10007]([c:10006]([c:10005]1[H:10015])[H:10016])[C:10010]([H:10019])([H:10020])[C:10011](=[O:10012])/[C:10013](=[C:10001](\[O-:10002])/[Cl:10003])/[H:10021])[H:10017])[H:10018].[H:14][c:4]1[c:9]([c:8]([c:7]([c:6]([c:5]1[H:15])[H:16])[C:10]([H:19])([H:20])[C:11](=[O:12])/[C:13](=[C:1](\[O-:2])/[Cl:3])/[H:21])[H:17])[H:18]
('2\tsp3\tNone\t2', '1\tsigma\t3\t2') ('10001\tpi\t10013\t2', '1\tsigma\t3\t2')
n_O > σ^*_C-Cl c1ccc(cc1)CC(=O)/C=C(\[O-])/Cl.c1ccc(cc1)CC(=O)/C=[C:20](\[O-:10])/[Cl:21]>>c1ccc(cc1)CC(=O)C=[C:20]=[O:10].c1ccc(cc1)CC(=O)/C=C(\[O-])/Cl.[Cl-:21] 10=20;20,21=21
π_C=C > σ^*_C-Cl c1ccc(cc1)CC(=O)/[CH:11]=[C:10](\[O-])/Cl.c1ccc(cc1)CC(=O)/C=[C:20](\[O-])/[Cl:21]>>c1ccc(cc1)CC(=O)/C=[C:20](/[C:10]([CH+:11]C(=O)Cc2ccccc2)([O-])Cl)\[O-].[Cl-:21] 10,11=10,20;20,21=21
139

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23]

[H:20][CH:21]([c:22]1[cH:23]cccc1)C(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=cc=[c:22]=[CH:21]C(=O)CC(=O)OC

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '18\tsigma\t8\t2; 9\tpi\t14\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > π^*_C-C [H:20][CH:21]([c:22]1[cH:23]cccc1)C(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc=cc=[c:22]=[CH:21]C(=O)CC(=O)OC 10=20;20,21=21,22;22,23=23
140

[H:20][c:21]1ccc[cH:23][c:22]1CC(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)C[c:22]1[cH-:23]ccc[c:21]1

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '24\tsigma\t14\t2; 9\tsigma\t10\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C:C [H:20][c:21]1ccc[cH:23][c:22]1CC(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)C[c:22]1[cH-:23]ccc[c:21]1 10=20;20,21=21,22;22,23=23
140

[H:21][c:20]1ccc(cc1)CC(=O)CC(=O)OC.[NH2-:10]>>[H-:21].COC(=O)CC(=O)Cc1cc[c:20](cc1)[NH2:10]

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '12\tsigma\t22\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-H [H:21][c:20]1ccc(cc1)CC(=O)CC(=O)OC.[NH2-:10]>>[H-:21].COC(=O)CC(=O)Cc1cc[c:20](cc1)[NH2:10] 10=20;20,21=21
140

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.COC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)Cc1ccccc1.CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23]

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.CO[C:11](=O)[CH2:10]C(=O)Cc1ccccc1.[NH2-]>>[H:20][CH2:10]C(=O)Cc1ccccc1.CO[C+:11]=O.CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-]

[H:10022][c:10012]1[c:10013]([c:10014]([c:10009]([c:10010]([c:10011]1[H:10021])[H:10020])[C:10008]([H:10018])([H:10019])[C:10006](=[O:10007])[C:10003]([H:10004])([H:10017])[C:10001](=[O:10002])[O:10015][C:10016]([H:10025])([H:10026])[H:10027])[H:10024])[H:10023].[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10003\tsigma\t10001\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.COC(=O)CC(=O)Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)Cc1ccccc1.CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.CO[C:11](=O)[CH2:10]C(=O)Cc1ccccc1.[NH2-]>>[H:20][CH2:10]C(=O)Cc1ccccc1.CO[C+:11]=O.CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
142

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23]

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:11](=O)[O:10]C.[NH2-]>>[H:20][O:10]C.c1ccc(cc1)C[C:22](=[CH:21][C+:11]=O)[O-:23].[NH2-]

[H:25][c:14]1[c:15]([c:16]([c:11]([c:12]([c:13]1[H:24])[H:23])[C:10]([H:21])([H:22])[C:1](=[O:2])[C:3]([H:4])([H:17])[C:6](=[O:7])[O:8][C:9]([H:18])([H:19])[H:20])[H:27])[H:26].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('8\tsigma\t6\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_O-C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[C:11](=O)[O:10]C.[NH2-]>>[H:20][O:10]C.c1ccc(cc1)C[C:22](=[CH:21][C+:11]=O)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
143

COC(=O)C[C:23](=O)[CH2:22][c:21]1[cH:20]cccc1.[NH2-:10]>>COC(=O)C[C-:23]=O.[CH2:22]=[c:21]=cc=cc=[cH:20][NH2:10]

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '14\tpi\t9\t2; 8\tsigma\t6\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > σ^*_C-C COC(=O)C[C:23](=O)[CH2:22][c:21]1[cH:20]cccc1.[NH2-:10]>>COC(=O)C[C-:23]=O.[CH2:22]=[c:21]=cc=cc=[cH:20][NH2:10] 10=20;20,21=21,22;22,23=23
145

COC(=O)CC(=O)Cc1ccc[cH:21][cH:20]1.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])CC(=O)CC(=O)OC

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '10\tpi\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C COC(=O)CC(=O)Cc1ccc[cH:21][cH:20]1.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])CC(=O)CC(=O)OC 10=20;20,21=21
145

COC(=O)CC(=O)Cc1cc[cH:21][cH:20]c1.[NH2-:10]>>COC(=O)CC(=O)Cc1cc[cH-:21][cH:20](c1)[NH2:10]

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '11\tsigma\t12\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C COC(=O)CC(=O)Cc1cc[cH:21][cH:20]c1.[NH2-:10]>>COC(=O)CC(=O)Cc1cc[cH-:21][cH:20](c1)[NH2:10] 10=20;20,21=21
145

COC(=O)CC(=O)Cc1cc[cH:20][cH:21]c1.[NH2-:10]>>COC(=O)CC(=O)Cc1c[cH-:21][cH:20](cc1)[NH2:10]

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '12\tsigma\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C COC(=O)CC(=O)Cc1cc[cH:20][cH:21]c1.[NH2-:10]>>COC(=O)CC(=O)Cc1c[cH-:21][cH:20](cc1)[NH2:10] 10=20;20,21=21
145

[H:20][c:21]1[cH:22][cH:23]cc(c1)CC(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)Cc1c[cH-:23][cH:22][c:21]c1

[H:22][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:21])[H:20])[C:8]([H:18])([H:19])[C:6](=[O:7])[C:3]([H:4])([H:17])[C:1](=[O:2])[O:15][C:16]([H:25])([H:26])[H:27])[H:24])[H:23].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '23\tsigma\t13\t2; 12\tsigma\t11\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])OC.[NH2-:10]>>[H:20][NH2:10].CO[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C:C [H:20][c:21]1[cH:22][cH:23]cc(c1)CC(=O)CC(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)CC(=O)Cc1c[cH-:23][cH:22][c:21]c1 10=20;20,21=21,22;22,23=23
145

[H:20][CH:21]([C:22](=[O:23])Cc1cc[cH:11][cH:10]c1)C(=O)OC.[NH2-]>>[H:20][cH:10]1cc(cc[cH+:11]1)C[C:22](=[CH:21]C(=O)OC)[O-:23].[NH2-]

[H:25][c:14]1[c:15]([c:16]([c:11]([c:12]([c:13]1[H:24])[H:23])[C:10]([H:21])([H:22])[C:1](=[O:2])[C:3]([H:4])([H:17])[C:6](=[O:7])[O:8][C:9]([H:18])([H:19])[H:20])[H:27])[H:26].[H:28][N-:5][H:29]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('13\tsigma\t14\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)C(=O)OC.[NH2-:10]>>[H:20][NH2:10].COC(=O)[CH:21]=[C:22](Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1cc[cH:11][cH:10]c1)C(=O)OC.[NH2-]>>[H:20][cH:10]1cc(cc[cH+:11]1)C[C:22](=[CH:21]C(=O)OC)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
148

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23]

C[N:21](C)[C:20](=O)CC(=O)Cc1ccccc1.[NH2-:10]>>C[N-:21]C.c1ccc(cc1)CC(=O)C[C:20](=O)[NH2:10]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '1\tsigma\t15\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-N C[N:21](C)[C:20](=O)CC(=O)Cc1ccccc1.[NH2-:10]>>C[N-:21]C.c1ccc(cc1)CC(=O)C[C:20](=O)[NH2:10] 10=20;20,21=21
150

[CH3:23][N:22](C)[C:21](=[O:20])CC(=O)Cc1ccccc1.[NH2-:10]>>[CH3-:23].C[N:22]=[C:21](CC(=O)Cc1ccccc1)[O:20][NH2:10]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '2\tpi\t1\t2; 15\tsigma\t16\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_O=C > σ^*_N-C [CH3:23][N:22](C)[C:21](=[O:20])CC(=O)Cc1ccccc1.[NH2-:10]>>[CH3-:23].C[N:22]=[C:21](CC(=O)Cc1ccccc1)[O:20][NH2:10] 10=20;20,21=21,22;22,23=23
150

[H:20][CH:21](C(=O)C[c:10]1cccc[cH:11]1)[C:22](=[O:23])N(C)C.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)CC(=O)[CH:21]=[C:22](N(C)C)[O-:23].[NH2-]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('9\tsigma\t10\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C[c:10]1cccc[cH:11]1)[C:22](=[O:23])N(C)C.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)CC(=O)[CH:21]=[C:22](N(C)C)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
150

[H:10][c:11]1ccccc1CC(=O)[CH:21]([H:20])[C:22](=[O:23])N(C)C.[NH2-]>>[H:10][H:20].CN(C)[C:22](=[CH:21]C(=O)Cc1cccc[c+:11]1)[O-:23].[NH2-]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('21\tsigma\t10\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > π^*_C=O [H:10][c:11]1ccccc1CC(=O)[CH:21]([H:20])[C:22](=[O:23])N(C)C.[NH2-]>>[H:10][H:20].CN(C)[C:22](=[CH:21]C(=O)Cc1cccc[c+:11]1)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
150

[H:20][c:21]1[cH:22][cH:23]c(cc1)CC(=O)CC(=O)N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)C(=O)CC(=O)C[c]1[cH-:23][cH:22][c:21]cc1

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '23\tsigma\t12\t2; 13\tsigma\t14\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > σ^*_C:C [H:20][c:21]1[cH:22][cH:23]c(cc1)CC(=O)CC(=O)N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)C(=O)CC(=O)C[c]1[cH-:23][cH:22][c:21]cc1 10=20;20,21=21,22;22,23=23
155

[H:23][c:22]1ccc[c:20]([cH:21]1)CC(=O)CC(=O)N(C)C.[NH2-:10]>>[H-:23].[cH:21]=[c:22]c=cc=[c:20](CC(=O)CC(=O)N(C)C)[NH2:10]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '9\tpi\t14\t2; 13\tsigma\t24\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > σ^*_C-H [H:23][c:22]1ccc[c:20]([cH:21]1)CC(=O)CC(=O)N(C)C.[NH2-:10]>>[H-:23].[cH:21]=[c:22]c=cc=[c:20](CC(=O)CC(=O)N(C)C)[NH2:10] 10=20;20,21=21,22;22,23=23
155

[H:20][CH:21](C(=O)C[c:11]1cccc[cH:10]1)[C:22](=[O:23])N(C)C.[NH2-]>>[H:20][cH:10]1cccc[c+:11]1CC(=O)[CH:21]=[C:22](N(C)C)[O-:23].[NH2-]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10\tsigma\t9\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
σ_C:C > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)C[c:11]1cccc[cH:10]1)[C:22](=[O:23])N(C)C.[NH2-]>>[H:20][cH:10]1cccc[c+:11]1CC(=O)[CH:21]=[C:22](N(C)C)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
155

[H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])[N:10](C)C.[NH2-]>>[H:20][N+:10](C)(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-]

[H:23][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:22])[H:21])[C:8]([H:19])([H:20])[C:6](=[O:7])[C:3]([H:4])([H:18])[C:1](=[O:2])[N:15]([C:16]([H:26])([H:27])[H:28])[C:17]([H:29])([H:30])[H:31])[H:25])[H:24].[H:32][N-:5][H:33]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('15\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])N(C)C.[NH2-:10]>>[H:20][NH2:10].CN(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C(=O)Cc1ccccc1)[C:22](=[O:23])[N:10](C)C.[NH2-]>>[H:20][N+:10](C)(C)[C:22](=[CH:21]C(=O)Cc1ccccc1)[O-:23].[NH2-] 10=20;20,21=21,22;22,23=23
155

[H:20][CH:21](C#N)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C#N)[O-:23]

c1ccc(cc1)C[C:23](=O)[CH2:22][C:21]#[N:20].[NH2-:10]>>[CH2:22]=[C:21]=[N:20][NH2:10].c1ccc(cc1)C[C-:23]=O

[H:20][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:19])[H:18])[C:8]([H:16])([H:17])[C:1](=[O:2])[C:3]([H:4])([H:15])[C:6]#[N:7])[H:22])[H:21].[H:23][N-:5][H:24]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '7\tpi\t6\t2; 3\tsigma\t1\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C#N)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C#N)[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_N#C > σ^*_C-C c1ccc(cc1)C[C:23](=O)[CH2:22][C:21]#[N:20].[NH2-:10]>>[CH2:22]=[C:21]=[N:20][NH2:10].c1ccc(cc1)C[C-:23]=O 10=20;20,21=21,22;22,23=23
160

[H:20][CH:21](C#N)[C:22](=[O:23])C[c:11]1[cH:10]cc[cH:13][cH:12]1.[NH2-]>>[H:20][cH:10]=cc=[cH+:13].[cH:12]=[c:11]C[C:22](=[CH:21]C#N)[O-:23].[NH2-]

[H:20][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:19])[H:18])[C:8]([H:16])([H:17])[C:1](=[O:2])[C:3]([H:4])([H:15])[C:6]#[N:7])[H:22])[H:21].[H:23][N-:5][H:24]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('14\tpi\t9\t2; 10\tpi\t11\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C#N)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C#N)[O-:23] 10=20;20,21=21,22;22,23=23
π_C-C > π_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21](C#N)[C:22](=[O:23])C[c:11]1[cH:10]cc[cH:13][cH:12]1.[NH2-]>>[H:20][cH:10]=cc=[cH+:13].[cH:12]=[c:11]C[C:22](=[CH:21]C#N)[O-:23].[NH2-] 10,11=10,20;12,13=11,12;20,21=21,22;22,23=23
160

[H:10][c:11]1ccc(cc1)C[C:22](=[O:23])[CH:21]([H:20])C#N.[NH2-]>>[H:10][H:20].c1cc(cc[c+:11]1)C[C:22](=[CH:21]C#N)[O-:23].[NH2-]

[H:20][c:12]1[c:13]([c:14]([c:9]([c:10]([c:11]1[H:19])[H:18])[C:8]([H:16])([H:17])[C:1](=[O:2])[C:3]([H:4])([H:15])[C:6]#[N:7])[H:22])[H:21].[H:23][N-:5][H:24]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('20\tsigma\t12\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21](C#N)[C:22](=[O:23])Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21]C#N)[O-:23] 10=20;20,21=21,22;22,23=23
σ_H-C > σ^*_H-C > π^*_C=O [H:10][c:11]1ccc(cc1)C[C:22](=[O:23])[CH:21]([H:20])C#N.[NH2-]>>[H:10][H:20].c1cc(cc[c+:11]1)C[C:22](=[CH:21]C#N)[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
160

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23]

c1ccc(cc1)C[C:20](=O)[CH2:21][N+](=O)[O-].[NH2-:10]>>[CH2-:21][N+](=O)[O-].c1ccc(cc1)C[C:20](=O)[NH2:10]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '1\tsigma\t3\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C-C c1ccc(cc1)C[C:20](=O)[CH2:21][N+](=O)[O-].[NH2-:10]>>[CH2-:21][N+](=O)[O-].c1ccc(cc1)C[C:20](=O)[NH2:10] 10=20;20,21=21
163

c1c[cH:23][c:22]([cH:21][cH:20]1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[cH-:23]=cc=[cH:20][NH2:10].[cH:21]=[c:22]CC(=O)C[N+](=O)[O-]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '9\tpi\t8\t2; 7\tpi\t12\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > π^*_C-C c1c[cH:23][c:22]([cH:21][cH:20]1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[cH-:23]=cc=[cH:20][NH2:10].[cH:21]=[c:22]CC(=O)C[N+](=O)[O-] 10=20;20,21=21,22;22,23=23
163

c1cc[c:21]([cH:20]c1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>c1cc[c-:21]([cH:20](c1)[NH2:10])CC(=O)C[N+](=O)[O-]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '8\tsigma\t7\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_C:C c1cc[c:21]([cH:20]c1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>c1cc[c-:21]([cH:20](c1)[NH2:10])CC(=O)C[N+](=O)[O-] 10=20;20,21=21
163

[H:23][c:22]1ccc[c:20]([cH:21]1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[H-:23].[cH:21]=[c:22]c=cc=[c:20](CC(=O)C[N+](=O)[O-])[NH2:10]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '7\tpi\t12\t2; 11\tsigma\t22\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_C-C > σ^*_C-H [H:23][c:22]1ccc[c:20]([cH:21]1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[H-:23].[cH:21]=[c:22]c=cc=[c:20](CC(=O)C[N+](=O)[O-])[NH2:10] 10=20;20,21=21,22;22,23=23
163

c1ccc(cc1)CC(=O)C[N+:20](=[O:21])[O-].[NH2-:10]>>c1ccc(cc1)CC(=O)C[N+:20]([NH2:10])([O-:21])[O-]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '13\tpi\t14\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > π^*_N=O c1ccc(cc1)CC(=O)C[N+:20](=[O:21])[O-].[NH2-:10]>>c1ccc(cc1)CC(=O)C[N+:20]([NH2:10])([O-:21])[O-] 10=20;20,21=21
163

c1ccc(cc1)CC(=O)C[N+:21](=O)[O-:20].[NH2-:10]>>c1ccc(cc1)CC(=O)C[N:21]=O.[NH2:10][O-:20]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('5\tsp3\tNone\t2', '15\tsigma\t13\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
n_N > σ^*_O-N c1ccc(cc1)CC(=O)C[N+:21](=O)[O-:20].[NH2-:10]>>c1ccc(cc1)CC(=O)C[N:21]=O.[NH2:10][O-:20] 10=20;20,21=21
163

[H:20][CH:21]([C:22](=[O:23])Cc1ccc[cH:11][cH:10]1)[N+](=O)[O-].[NH2-]>>[H:20][cH:10]=c(c=cc=[cH+:11])C[C:22](=[CH:21][N+](=O)[O-])[O-:23].[NH2-]

[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('8\tpi\t9\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
π_C-C > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccc[cH:11][cH:10]1)[N+](=O)[O-].[NH2-]>>[H:20][cH:10]=c(c=cc=[cH+:11])C[C:22](=[CH:21][N+](=O)[O-])[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
163

[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].c1ccc(cc1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)C[N+](=O)[O-].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23]

[H:11][CH:10](C(=O)Cc1ccccc1)[N+](=O)[O-].[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-]>>[H+:11].[H:20][CH:10](C(=O)Cc1ccccc1)[N+](=O)[O-].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23].[NH2-]

[H:10021][c:10010]1[c:10011]([c:10012]([c:10007]([c:10008]([c:10009]1[H:10020])[H:10019])[C:10006]([H:10017])([H:10018])[C:10001](=[O:10002])[C:10003]([H:10004])([H:10016])[N+:10013](=[O:10014])[O-:10015])[H:10023])[H:10022].[H:21][c:10]1[c:11]([c:12]([c:7]([c:8]([c:9]1[H:20])[H:19])[C:6]([H:17])([H:18])[C:1](=[O:2])[C:3]([H:4])([H:16])[N+:13](=[O:14])[O-:15])[H:23])[H:22].[H:24][N-:5][H:25]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2') ('10003\tsigma\t10004\t2', '4\tsigma\t3\t2; 1\tpi\t2\t2')
n_N > σ^*_H-C > π^*_C=O [H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].c1ccc(cc1)CC(=O)C[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].c1ccc(cc1)CC(=O)C[N+](=O)[O-].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23] 10=20;20,21=21,22;22,23=23
σ_C-H > σ^*_H-C > π^*_C=O [H:11][CH:10](C(=O)Cc1ccccc1)[N+](=O)[O-].[H:20][CH:21]([C:22](=[O:23])Cc1ccccc1)[N+](=O)[O-].[NH2-]>>[H+:11].[H:20][CH:10](C(=O)Cc1ccccc1)[N+](=O)[O-].c1ccc(cc1)C[C:22](=[CH:21][N+](=O)[O-])[O-:23].[NH2-] 10,11=10,20;20,21=21,22;22,23=23
165

C(C#N)[N+:21](=[O:20])[O-].[NH2-:10]>>C(C#N)[N:21]([O-])[O:20][NH2:10]

[H:4][C:3]([H:9])([C:1]#[N:2])[N+:6](=[O:7])[O-:8].[H:10][N-:5][H:11]
('5\tsp3\tNone\t2', '4\tsigma\t3\t2') ('5\tsp3\tNone\t2', '7\tpi\t6\t2')
n_N > σ^*_H-C [H:20][CH:21](C#N)[N+](=O)[O-].[NH2-:10]>>[H:20][NH2:10].[CH-:21](C#N)[N+](=O)[O-] 10=20;20,21=21
n_N > π^*_O=N C(C#N)[N+:21](=[O:20])[O-].[NH2-:10]>>C(C#N)[N:21]([O-])[O:20][NH2:10] 10=20;20,21=21
166

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$ $CC(=O)/C=[C:20](/[CH2:21]c1ccccc1)\O.[NH2-:10]>>CC(=O)/C=[C:20](\[NH2:10])/O.[CH2-:21]c1ccccc1$
[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('5\tsp3\tNone\t2', '1\tsigma\t9\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
n_N > σ^*_C-C CC(=O)/C=[C:20](/[CH2:21]c1ccccc1)\O.[NH2-:10]>>CC(=O)/C=[C:20](\[NH2:10])/O.[CH2-:21]c1ccccc1 10=20;20,21=21
169

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$ $[H:21][CH:20](c1ccccc1)/C(=C/C(=O)C)/O.[NH2-:10]>>[H-:21].CC(=O)/C=C(/[CH:20](c1ccccc1)[NH2:10])\O$
[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('5\tsp3\tNone\t2', '9\tsigma\t20\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
n_N > σ^*_C-H [H:21][CH:20](c1ccccc1)/C(=C/C(=O)C)/O.[NH2-:10]>>[H-:21].CC(=O)/C=C(/[CH:20](c1ccccc1)[NH2:10])\O 10=20;20,21=21
169

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$ $CC(=O)/C=C(/Cc1ccc[cH:21][cH:20]1)\O.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])C/C(=C/C(=O)C)/O$
[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('5\tsp3\tNone\t2', '11\tpi\t12\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
n_N > π^*_C-C CC(=O)/C=C(/Cc1ccc[cH:21][cH:20]1)\O.[NH2-:10]>>[cH-:21]=cc=cc(=[cH:20][NH2:10])C/C(=C/C(=O)C)/O 10=20;20,21=21
169

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$

[H:20][c:21]1[cH:22][cH:23]cc(c1)C/C(=C/C(=O)C)/O.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc(=c[c:21]=[cH:22])C/C(=C/C(=O)C)/O

[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('5\tsp3\tNone\t2', '23\tsigma\t12\t2; 13\tpi\t14\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
n_N > σ^*_H-C > π^*_C-C [H:20][c:21]1[cH:22][cH:23]cc(c1)C/C(=C/C(=O)C)/O.[NH2-:10]>>[H:20][NH2:10].[cH-:23]=cc(=c[c:21]=[cH:22])C/C(=C/C(=O)C)/O 10=20;20,21=21,22;22,23=23
169

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$ $[H:20][O:21]/[C:11](=[CH:10]\C(=O)C)/[CH2:12][c:13]1ccccc1.[NH2-]>>[H:20][CH:10](C(=O)C)[C:11](=[CH2:12])[O-:21].c1cc[c+:13]cc1.[NH2-]$
[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('3\tpi\t1\t2; 9\tsigma\t10\t2', '4\tsigma\t2\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
σ_C-C > π_C=C > σ^*_H-O [H:20][O:21]/[C:11](=[CH:10]\C(=O)C)/[CH2:12][c:13]1ccccc1.[NH2-]>>[H:20][CH:10](C(=O)C)[C:11](=[CH2:12])[O-:21].c1cc[c+:13]cc1.[NH2-] 10,11=10,20;12,13=11,12;20,21=21
169

$[H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21]$ $[H:20][O:21]/C(=C\C(=O)C)/C[c:10]1cccc[cH:11]1.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)C/C(=C/C(=O)C)/[O-:21].[NH2-]$
[H:24][c:13]1[c:14]([c:15]([c:10]([c:11]([c:12]1[H:23])[H:22])[C:9]([H:20])([H:21])/[C:1](=[C:3](\[H:16])/[C:6](=[O:7])[C:8]([H:17])([H:18])[H:19])/[O:2][H:4])[H:26])[H:25].[H:27][N-:5][H:28]
('5\tsp3\tNone\t2', '4\tsigma\t2\t2') ('10\tsigma\t11\t2', '4\tsigma\t2\t2')
n_N > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/Cc1ccccc1.[NH2-:10]>>[H:20][NH2:10].CC(=O)/C=C(/Cc1ccccc1)\[O-:21] 10=20;20,21=21
σ_C:C > σ^*_H-O [H:20][O:21]/C(=C\C(=O)C)/C[c:10]1cccc[cH:11]1.[NH2-]>>[H:20][c:10]1(cccc[cH+:11]1)C/C(=C/C(=O)C)/[O-:21].[NH2-] 10,11=10,20;20,21=21
169