Mayr's Database of Reactivity Parameters

Arenes

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles
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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
toluene
C7H8*
 dichloromethane

N  Param.: -4.36

sN Param.: 1.77		*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
m-xylene
C8H10*
 dichloromethane

N  Param.: -3.57

sN Param.: 2.08		*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methylthiophene
C5H6S*
 dichloromethane

N  Param.: 1.35

sN Param.: 0.99		*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
1,3-dimethoxybenzene
C8H10O2*
 dichloromethane

N  Param.: 2.48

sN Param.: 1.09		*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methylfuran
C5H6O*
 dichloromethane

N  Param.: 3.61

sN Param.: 1.11		*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-methylpyrrole
C5H7N*
 dichloromethane

N  Param.: 5.85

sN Param.: 1.03		*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
3-methylanisole
C8H10O*
 dichloromethane

N  Param.: 0.13

sN Param.: 1.27		***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
furan
C4H4O*
 dichloromethane

N  Param.: 1.33

sN Param.: 1.29		*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
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
3-methoxythiophene
C5H6OS*
 MeCN

N  Param.: 3.06

sN Param.: 1.19		***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
2,5-dimethylpyrrole
C6H9N*
 MeCN

N  Param.: 8.01

sN Param.: 0.96		***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
1,2,5-trimethylpyrrole
C7H11N*
 MeCN

N  Param.: 8.69

sN Param.: 1.07		***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
2,4-dimethylpyrrole
C6H9N*
 MeCN

N  Param.: 10.67

sN Param.: 0.91		***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
3-ethyl-2,4-dimethylpyrrole
C8H13N*
 MeCN

N  Param.: 11.63

sN Param.: 0.95		***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
azulene
C10H8*
 MeCN

N  Param.: 6.66

sN Param.: 1.02		***Eur. J. Org. Chem. 2009, , 1202-1206
10.1002/ejoc.200801099
N-(triisopropylsilyl)pyrrole
C13H25NSi*
 dichloromethane

N  Param.: 3.12

sN Param.: 0.93		***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
pyrrole
C4H5N*
 dichloromethane

N  Param.: 4.63

sN Param.: 1.00		*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
2-(trimethylsilyl)furan
C7H12OSi*
 dichloromethane

N  Param.: 2.16

sN Param.: 1.10		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(triethylsilyl)furan
C10H18OSi*
 dichloromethane

N  Param.: 2.20

sN Param.: 1.10		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylsilyl)furan
C16H30OSi*
 dichloromethane

N  Param.: 2.37

sN Param.: 1.10		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
thiophene
C4H4S*
 dichloromethane

N  Param.: -1.01

sN Param.: 1.10		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(trimethylsilyl)thiophene
C7H12SSi*
 dichloromethane

N  Param.: -0.80

sN Param.: 1.00		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylstannyl)furan
C16H30OSn*
 dichloromethane

N  Param.: 3.63

sN Param.: 1.10		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylstannyl)thiophene
C16H30SSn*
 dichloromethane

N  Param.: 1.53

sN Param.: 1.00		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
anisole
C7H8O*
 dichloromethane

N  Param.: -1.18

sN Param.: 1.20		*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c