Mayr's Database of Reactivity Parameters

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