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
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
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
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
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
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
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 water)
C6H7N *
 water

N  Param.: 12.99

sN Param.: 0.73		 *** 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 water)
C7H9N *
 water

N  Param.: 13.00

sN Param.: 0.79		 *** 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
4-methoxyaniline (in water)
C7H9NO *
 water

N  Param.: 14.28

sN Param.: 0.68		 *** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
4-methoxyaniline (in MeCN)
C7H9NO *
 MeCN

N  Param.: 13.42

sN Param.: 0.73		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
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
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
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
cyanate (in MeCN)
CNO- *
 MeCN

N  Param.: 13.60

sN Param.: 0.84		 *** Chem. Eur. J. 2008, 14, 3866-3868
10.1002/chem.200800314