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)
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
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
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 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
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 H2O)
C7H10N2 *
 water

N  Param.: 13.19

sN Param.: 0.56		 *** 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
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
glycinenitrile (in water)
*
 water

N  Param.: 10.80

sN Param.: 0.61		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethanolamine (in water)
C2H7NO *
 water

N  Param.: 12.61

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethylenediamine (in water)
C2H8N2 *
 water

N  Param.: 13.28

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
propargylamine (in water)
C3H5N *
 water

N  Param.: 12.29

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
allylamine (in water)
C3H7N *
 water

N  Param.: 13.21

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
benzylamine (in water)
C7H9N *
 water

N  Param.: 13.44

sN Param.: 0.55		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
aniline (in water)
C6H7N *
 water

N  Param.: 12.99

sN Param.: 0.73		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
p-toluidine (in water)
C7H9N *
 water

N  Param.: 13.00

sN Param.: 0.79		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
4-methoxyaniline (in water)
C7H9NO *
 water

N  Param.: 14.28

sN Param.: 0.68		 *** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
diethanolamine (in water)
C4H11NO2 *
 water

N  Param.: 13.00

sN Param.: 0.61		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
N-methyl-glycinenitrile (in water)
C3H6N2 *
 water

N  Param.: 13.50

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
methyl glycinate (in water)
C3H7NO2 *
 water

N  Param.: 12.08

sN Param.: 0.60		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
glycineamide (in water)
C2H6N2O *
 water

N  Param.: 12.29

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
1,3-diaminopropane (in water)
C3H10N2 *
 water

N  Param.: 14.02

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
glycine (anionic, in water)
C2H4NO2 *
 water

N  Param.: 13.51

sN Param.: 0.58		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
alanine (anionic, in water)
C3H6NO2 *
 water

N  Param.: 13.01

sN Param.: 0.58		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
valine (anionic, in water)
C5H10NO2 *
 water

N  Param.: 13.65

sN Param.: 0.57		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
leucine (anionic, in water)
C6H12NO2 *
 water

N  Param.: 14.01

sN Param.: 0.52		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
phenylalanine (anionic, in water)
C9H10NO2 *
 water

N  Param.: 14.12

sN Param.: 0.53		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
proline (anionic, in water)
C5H8NO2 *
 water

N  Param.: 18.08

sN Param.: 0.50		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
serine (anionic, in water)
C3H6NO3 *
 water

N  Param.: 13.16

sN Param.: 0.55		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
threonine (anionic, in water)
C4H8NO3 *
 water

N  Param.: 12.69

sN Param.: 0.60		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
asparagine (anionic, in water)
C4H7N2O3 *
 water

N  Param.: 13.03

sN Param.: 0.53		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
glutamine (anionic, in water)
C5H9N2O3 *
 water

N  Param.: 13.45

sN Param.: 0.54		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
arginine (betaine, in water)
C6H14N4O2 *
 water

N  Param.: 12.96

sN Param.: 0.57		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
histidine (anionic, in water)
C6H8N3O2 *
 water

N  Param.: 13.83

sN Param.: 0.54		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
aspartate (dianionic, in water)
C4H5NO4 *
 water

N  Param.: 13.81

sN Param.: 0.53		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
glutamate (dianionic, in water)
C5H7NO4 *
 water

N  Param.: 13.96

sN Param.: 0.54		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
cysteine (dianionic, in water, S-nucleophile!)
C3H5NO2S *
 water

N  Param.: 23.43

sN Param.: 0.42		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
methionine (anionic, in water)
C5H10NO2S *
 water

N  Param.: 13.16

sN Param.: 0.58		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
beta-alanine (anionic, in water)
C3H6NO2 *
 water

N  Param.: 13.26

sN Param.: 0.58		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
gamma-aminobutyric acid (anionic, in water)
C4H8NO2 *
 water

N  Param.: 13.55

sN Param.: 0.56		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
glycylglycine (anionic, in water)
C4H7N2O3 *
 water

N  Param.: 12.91

sN Param.: 0.59		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
glycylglycylglycine (anionic, in water)
C6H10N3O4 *
 water

N  Param.: 12.26

sN Param.: 0.63		 *** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
imidazole (in water)
*
 water

N  Param.: 9.63

sN Param.: 0.57		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-imidazole (in water)
*
 water

N  Param.: 9.91

sN Param.: 0.55		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-imidazole (in water)
*
 water

N  Param.: 9.45

sN Param.: 0.54		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-pyridone anion (in water)
*
 water

N  Param.: 12.47

sN Param.: 0.52		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
4-pyridone anion (in water)
*
 water

N  Param.: 14.76

sN Param.: 0.48		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
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
hydrazine (in water)
*
 water

N  Param.: 13.46

sN Param.: 0.57		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
methylhydrazine (in water)
*
 water

N  Param.: 17.23

sN Param.: 0.45		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
2-phenylethylamine (in water)
C8H11N *
 water

N  Param.: 13.40

sN Param.: 0.57		 *** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
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
Se-HyperBTM (in THF)
C19H20N2Se *
 THF

N  Param.: 14.19

sN Param.: 0.77		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
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 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 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
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
thiocyanate (in MeCN)
CNS *
 MeCN

N  Param.: 12.13

sN Param.: 0.60		 * J. Am. Chem. Soc. 2003, 125, 14126-14132
10.1021/ja037317u
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
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-chloroaniline (in MeCN)
C6H6ClN *
 MeCN

N  Param.: 12.92

sN Param.: 0.60		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
aniline (in MeCN)
C6H7N *
 MeCN

N  Param.: 12.64

sN Param.: 0.68		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
p-toluidine (in MeCN)
C7H9N *
 MeCN

N  Param.: 13.19

sN Param.: 0.69		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z