Mayr's Database of Reactivity Parameters

Indoles

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles » Arenes
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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
Indole
C8H7N*
 dichloromethane

N  Param.: 5.55

sN Param.: 1.09		***J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
N-methylindole
C9H9N*
 dichloromethane

N  Param.: 5.75

sN Param.: 1.23		***J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1,2-dimethylindole
C10H11N*
 dichloromethane

N  Param.: 6.54

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-methoxy-indole
C9H9NO*
 dichloromethane

N  Param.: 6.22

sN Param.: 1.12		***J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-amino-indole
C8H8N2*
 MeCN

N  Param.: 7.22

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-hydroxy-indole
C8H7NO*
 MeCN

N  Param.: 6.44

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-methyl-indole
C9H9N*
 MeCN

N  Param.: 6.00

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-chloro-indole
C8H6ClN*
 MeCN

N  Param.: 4.42

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-bromo-indole
C8H6BrN*
 MeCN

N  Param.: 4.38

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-cyano-indole
C9H6N2*
 MeCN

N  Param.: 2.83

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1H-indole-5-carboxylic acid
C9H7NO2*
 MeCN

N  Param.: 3.97

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-methoxy-2-methylindole
C10H11NO*
 MeCN

N  Param.: 7.26

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
2,5-dimethylindole
C10H11N*
 MeCN

N  Param.: 7.22

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
2-methylindole
C9H9N*
 MeCN

N  Param.: 6.91

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-chloro-2-methylindole
C9H8ClN*
 MeCN

N  Param.: 6.08

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
4-methoxy-indole
C9H9NO*
 MeCN

N  Param.: 5.41

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
7-azaindole
C7H6N2*
 MeCN

N  Param.: 3.87

sN Param.: 1.10		*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
tert-butyl indole-1-carboxylate
C13H15NO2*
 MeCN

N  Param.: 1.68

sN Param.: 1.26		***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655