Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
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
DABCO (in MeCN)
C6H12N2*
MeCN

N  Param.: 18.80

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
quinuclidine (in MeCN)
C7H13N*
MeCN

N  Param.: 20.54

sN Param.: 0.60
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
hydrazine (in MeCN)
*
MeCN

N  Param.: 16.45

sN Param.: 0.56
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 11.72

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
trimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 12.43

sN Param.: 0.75
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 22.41

sN Param.: 0.45
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
trimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 17.75

sN Param.: 0.53
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
4-(dimethylamino)pyridine (in THF)
*
THF

N  Param.: 15.90

sN Param.: 0.66
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
DBU (in THF)
*
THF

N  Param.: 16.12

sN Param.: 0.67
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2*
dichloromethane

N  Param.: 19.31

sN Param.: 0.46
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 17.90

sN Param.: 0.48
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
DBU (in MeCN)
C9H16N2*
MeCN

N  Param.: 15.29

sN Param.: 0.70
***Chem. Commun. 2008, , 1792-1794
10.1039/b801811a
DBN (in MeCN)
C7H12N2*
MeCN

N  Param.: 16.28

sN Param.: 0.67
***Chem. Commun. 2008, , 1792-1794
10.1039/b801811a
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 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
cyanate (in MeCN)
CNO-*
MeCN

N  Param.: 13.60

sN Param.: 0.84
***Chem. Eur. J. 2008, 14, 3866-3868
10.1002/chem.200800314
imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.09

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.03

sN Param.: 0.50
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.29

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2,4-dimethyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 20.69

sN Param.: 0.60
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-nitro-imidazole anion (in DMSO)
*
DMSO

N  Param.: 14.81

sN Param.: 0.71
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-formyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 16.06

sN Param.: 0.68
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-formyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 16.40

sN Param.: 0.67
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
benzimidazole anion (in DMSO)
*
DMSO

N  Param.: 19.13

sN Param.: 0.55
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
benzotriazole anion (in DMSO)
*
DMSO

N  Param.: 16.29

sN Param.: 0.65
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
purine anion (in DMSO)
*
DMSO

N  Param.: 15.03

sN Param.: 0.77
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
theophylline anion (in DMSO)
*
DMSO

N  Param.: 14.78

sN Param.: 0.71
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
adenine anion (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.55
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
uracil anion (in DMSO)
*
DMSO

N  Param.: 17.04

sN Param.: 0.63
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
thymine anion (in DMSO)
*
DMSO

N  Param.: 17.63

sN Param.: 0.62
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1-methyl uracil anion (in DMSO)
*
DMSO

N  Param.: 16.36

sN Param.: 0.69
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-nitro-imidazole anion (in water)
*
water

N  Param.: 11.37

sN Param.: 0.53
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-formyl-imidazole anion (in water)
*
water

N  Param.: 11.07

sN Param.: 0.50
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
benzotriazole anion (in water)
*
water

N  Param.: 11.52

sN Param.: 0.67
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
purine anion (in water)
*
water

N  Param.: 11.00

sN Param.: 0.54
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
theophylline anion (in water)
*
water

N  Param.: 10.06

sN Param.: 0.71
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
adenine anion (in water)
*
water

N  Param.: 10.93

sN Param.: 0.62
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
guanine anion (in water)
*
water

N  Param.: 11.63

sN Param.: 0.59
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
9-methyl guanine anion (in water)
*
water

N  Param.: 10.77

sN Param.: 0.65
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
guanosine anion (in water)
*
water

N  Param.: 12.09

sN Param.: 0.52
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
uracil anion (in water)
*
water

N  Param.: 10.75

sN Param.: 0.53
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
thymine anion (in water)
*
water

N  Param.: 11.17

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1-methyl uracil anion (in water)
*
water

N  Param.: 8.54

sN Param.: 0.77
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1,1,3,3-tetramethylguanidine
C5H13N3*
dichloromethane

N  Param.: 13.58

sN Param.: 0.77
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-benzyl-1,1,3,3-tetramethylguanidine
C12H19N3*
dichloromethane

N  Param.: 14.36

sN Param.: 0.79
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,3-dimethylimidazolidin-2-imine
C5H11N3*
dichloromethane

N  Param.: 12.46

sN Param.: 0.87
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine
C12H17N3*
dichloromethane

N  Param.: 14.00

sN Param.: 0.70
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)
C5H9N3*
dichloromethane

N  Param.: 14.44

sN Param.: 0.79
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
C6H11N3*
dichloromethane

N  Param.: 16.15

sN Param.: 0.73
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
C8H15N3*
dichloromethane

N  Param.: 14.43

sN Param.: 0.81
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
C7H13N3*
dichloromethane

N  Param.: 16.16

sN Param.: 0.75
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
DBN (in CH2Cl2)
*
dichloromethane

N  Param.: 15.50

sN Param.: 0.76
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
4-methoxyaniline (in water)
C7H9NO*
water

N  Param.: 14.28

sN Param.: 0.68
***ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
2-phenylethylamine (in water)
C8H11N*
water

N  Param.: 13.40

sN Param.: 0.57
***ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
2,2,2-trifluoroethylamine (in MeCN)
*
MeCN

N  Param.: 10.13

sN Param.: 0.75
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
tert-butylamine (in MeCN)
*
MeCN

N  Param.: 12.35

sN Param.: 0.72
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
isopropylamine (in MeCN)
*
MeCN

N  Param.: 13.77

sN Param.: 0.70
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
ethanolamine (in MeCN)
*
MeCN

N  Param.: 14.11

sN Param.: 0.71
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
benzylamine (in MeCN)
*
MeCN

N  Param.: 14.29

sN Param.: 0.67
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
allylamine (in MeCN)
*
MeCN

N  Param.: 14.37

sN Param.: 0.66
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
n-propylamine (in MeCN)
*
MeCN

N  Param.: 15.11

sN Param.: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
n-butylamine (in MeCN)
*
MeCN

N  Param.: 15.27

sN Param.: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
dipropylamine (in MeCN)
*
MeCN

N  Param.: 14.51

sN Param.: 0.80
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
diethylamine (in MeCN)
*
MeCN

N  Param.: 15.10

sN Param.: 0.73
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
morpholine (in MeCN)
*
MeCN

N  Param.: 15.65

sN Param.: 0.74
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
piperidine (in MeCN)
*
MeCN

N  Param.: 17.35

sN Param.: 0.68
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
pyrrolidine (in MeCN)
*
MeCN

N  Param.: 18.64

sN Param.: 0.60
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
di(methoxyethyl)amine (in MeCN)
*
MeCN

N  Param.: 13.24

sN Param.: 0.93
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C4H8N2*
dichloromethane

N  Param.: 12.92

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C9H10N2*
dichloromethane

N  Param.: 12.31

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)
C6H10N2O*
dichloromethane

N  Param.: 10.03

sN Param.: 0.75
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C16H16N2*
dichloromethane

N  Param.: 13.11

sN Param.: 0.83
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydrothiazole (in CH2Cl2)
C4H7NS*
dichloromethane

N  Param.: 10.20

sN Param.: 0.71
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213