Mayr's Database of Reactivity Parameters

N-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles » N-Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
thiocyanate (in MeCN)
CNS *
 MeCN

N  Param.: 12.13

sN Param.: 0.60		 * J. Am. Chem. Soc. 2003, 125, 14126-14132
10.1021/ja037317u
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
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-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-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-(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
5-methoxy-benzimidazole (in DMSO)
*
 DMSO

N  Param.: 11.00

sN Param.: 0.71		 * Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
benzotriazole (in MeCN)
*
 MeCN

N  Param.: 7.69

sN Param.: 0.76		 * Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-benzotriazole (in MeCN)
*
 MeCN

N  Param.: 7.77

sN Param.: 0.76		 * Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
triethylamine (in MeCN)
*
 MeCN

N  Param.: 17.10

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
triethylamine (in CH2Cl2)
*
 dichloromethane

N  Param.: 17.30

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
N-methyl-pyrrolidine (in CH2Cl2)
*
 dichloromethane

N  Param.: 20.60

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
N-methyl-piperidine (in CH2Cl2)
*
 dichloromethane

N  Param.: 18.90

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
N-methyl-morpholine (in MeCN)
*
 MeCN

N  Param.: 16.80

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
N-methyl-morpholine (in CH2Cl2)
*
 dichloromethane

N  Param.: 16.50

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)
C14H13N *
 dichloromethane

N  Param.: 7.90

sN Param.: 0.76		 ** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
semicarbazide (in water)
CH5N3O *
 water

N  Param.: 11.05

sN Param.: 0.52		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
hydroxylamine (in water)
H3NO *
 water

N  Param.: 11.41

sN Param.: 0.55		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,2-trifluoroethylamine (in DMSO)
C2H4F3N *
 DMSO

N  Param.: 12.15

sN Param.: 0.65		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in water)
C3H9N *
 water

N  Param.: 13.33

sN Param.: 0.56		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ethyl glycinate (in DMSO)
C4H9NO2 *
 DMSO

N  Param.: 14.30

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in DMSO)
C3H9N *
 DMSO

N  Param.: 15.70

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
morpholine (in DMSO)
C4H9NO *
 DMSO

N  Param.: 16.96

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
piperidine (in DMSO)
C5H11N *
 DMSO

N  Param.: 17.19

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
nitrite ion (in MeCN)
NO2 *
 MeCN

N  Param.: 17.20

sN Param.: 0.72		 *** Angew. Chem. Int. Ed. 2005, 44, 4623-4626
10.1002/anie.200501274
azide ion (in 91M9AN)
N3- *
 MeOH-MeCN mix

N  Param.: 14.54

sN Param.: 0.82		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91E9AN)
N3- *
 EtOH-MeCN mix

N  Param.: 16.30

sN Param.: 0.73		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91nPr9AN)
N3- *
 nPrOH-MeCN mix

N  Param.: 16.70

sN Param.: 0.73		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91iPr9AN)
N3- *
 iPrOH-MeCN mix

N  Param.: 17.07

sN Param.: 0.71		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in DMSO)
N3- *
 DMSO

N  Param.: 20.50

sN Param.: 0.59		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 45M55AN)
N3- *
 MeOH-MeCN mix

N  Param.: 15.01

sN Param.: 0.80		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
pyrrolidine (in 91M9AN)
C4H9N *
 MeOH-MeCN mix

N  Param.: 15.97

sN Param.: 0.63		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
piperidine (in 91M9AN)
C5H11N *
 MeOH-MeCN mix

N  Param.: 15.63

sN Param.: 0.64		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
morpholine (in 91M9AN)
C4H9NO *
 MeOH-MeCN mix

N  Param.: 15.40

sN Param.: 0.64		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
diethanolamine (in 91M9AN)
C4H11NO2 *
 MeOH-MeCN mix

N  Param.: 13.71

sN Param.: 0.67		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
hydrazine (in 91M9AN)
H4N2 *
 MeOH-MeCN mix

N  Param.: 13.47

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
2,2,2-trifluoroethylamine (in 91M9AN)
C2H4F3N *
 MeOH-MeCN mix

N  Param.: 10.20

sN Param.: 0.92		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
imidazole (in 91M9AN)
C3H4N2 *
 MeOH-MeCN mix

N  Param.: 10.41

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
hydroxylamine (in 91M9AN)
H3NO *
 MeOH-MeCN mix

N  Param.: 12.23

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
ethanolamine (in 91M9AN)
C2H7NO *
 MeOH-MeCN mix

N  Param.: 13.23

sN Param.: 0.65		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
benzylamine (in 91M9AN)
C7H9N *
 MeOH-MeCN mix

N  Param.: 13.46

sN Param.: 0.62		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
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
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 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 H2O)
C6H7NO *
 water

N  Param.: 11.44

sN Param.: 0.68		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941