Mayr's Database of Reactivity Parameters

Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
n-propylamine (in 91M9AN)
C3H9N *
 MeOH-MeCN mix

N  Param.: 13.41

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
4-chloropyridine (in CH2Cl2)
C5H4ClN *
 dichloromethane

N  Param.: 11.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-chloropyridine (in H2O)
C5H4ClN *
 water

N  Param.: 10.50

sN Param.: 0.73		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
pyridine (in CH2Cl2)
C5H5N *
 dichloromethane

N  Param.: 12.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
pyridine (in H2O)
C5H5N *
 water

N  Param.: 11.05

sN Param.: 0.73		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methylpyridine (in CH2Cl2)
C6H7N *
 dichloromethane

N  Param.: 13.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methylpyridine (in H2O)
C6H7N *
 water

N  Param.: 11.10

sN Param.: 0.75		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methoxypyridine (in CH2Cl2)
C6H7NO *
 dichloromethane

N  Param.: 13.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methoxypyridine (in H2O)
C6H7NO *
 water

N  Param.: 11.44

sN Param.: 0.68		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-aminopyridine (in CH2Cl2)
C5H6N2 *
 dichloromethane

N  Param.: 15.20

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-aminopyridine (in H2O)
C5H6N2 *
 water

N  Param.: 12.19

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in CH2Cl2)
C7H10N2 *
 dichloromethane

N  Param.: 15.80

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in MeCN)
C7H10N2 *
 MeCN

N  Param.: 15.51

sN Param.: 0.62		 *** J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
4-(dimethylamino)pyridine (in H2O)
C7H10N2 *
 water

N  Param.: 13.19

sN Param.: 0.56		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in 91M9AN)
C7H10N2 *
 MeOH-MeCN mix

N  Param.: 13.20

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMSO)
C7H10N2 *
 DMSO

N  Param.: 14.80

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMF)
C7H10N2 *
 DMF

N  Param.: 14.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-pyrrolidinopyridine (in CH2Cl2)
C9H12N2 *
 dichloromethane

N  Param.: 15.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-pyrrolidinopyridine (in H2O)
C9H12N2 *
 water

N  Param.: 12.39

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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 isocyanide
C5H9N *
 dichloromethane

N  Param.: 5.47

sN Param.: 0.77		 *** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
benzyl isocyanide
C8H7N *
 dichloromethane

N  Param.: 4.90

sN Param.: 0.74		 *** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
2,6-dimethylphenyl isocyanide
C9H9N *
 dichloromethane

N  Param.: 4.59

sN Param.: 0.87		 *** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
p-tosylmethyl isocyanide (TosMIC)
C9H9NO2S *
 dichloromethane

N  Param.: 3.50

sN Param.: 0.76		 *** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
4-cyanophenyl isocyanide
C8H4N2 *
 dichloromethane

N  Param.: 3.57

sN Param.: 0.72		 ** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
ammonia (in water)
H3N *
 water

N  Param.: 9.48

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
methylamine (in water)
CH5N *
 water

N  Param.: 13.85

sN Param.: 0.53		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethylamine (in water)
C2H7N *
 water

N  Param.: 12.87

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
isopropylamine (in water)
C3H9N *
 water

N  Param.: 12.00

sN Param.: 0.56		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
tert-butylamine (in water)
C4H11N *
 water

N  Param.: 10.48

sN Param.: 0.65		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
dimethylamine (in water)
C2H7N *
 water

N  Param.: 17.12

sN Param.: 0.50		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
diethylamine (in water)
C4H11N *
 water

N  Param.: 14.68

sN Param.: 0.53		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyrrolidine (in water)
C4H9N *
 water

N  Param.: 17.21

sN Param.: 0.49		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
piperidine (in water)
C5H11N *
 water

N  Param.: 18.13

sN Param.: 0.44		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
morpholine (in water)
C4H9NO *
 water

N  Param.: 15.62

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
piperazine (in water)
C4H10N2 *
 water

N  Param.: 17.22

sN Param.: 0.50		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
perhydroazepine (in water)
C6H13N *
 water

N  Param.: 18.29

sN Param.: 0.46		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z