Mayr's Database of Reactivity Parameters

N-Nucleophiles

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

N  Param.: 2.23

sN Param.: 0.84
***J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
C15H22N2O*
MeCN

N  Param.: 5.44

sN Param.: 1.12
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one
C13H18N2O*
MeCN

N  Param.: 6.04

sN Param.: 0.92
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
C16H18N2O2*
MeCN

N  Param.: 7.39

sN Param.: 1.00
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
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
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
N-methyl-1-phenylmethanimine (in CH2Cl2)
C8H9N*
dichloromethane

N  Param.: 8.60

sN Param.: 0.77
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
C16H18N2O2*
MeCN

N  Param.: 8.76

sN Param.: 0.89
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
N-phenylcyclohexanimine (in CH2Cl2)
C12H15N*
dichloromethane

N  Param.: 8.80

sN Param.: 1.00
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
2-tritylpyrrolidine
C23H23N*
MeCN

N  Param.: 9.16

sN Param.: 1.39
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-methyl-imidazole (in water)
*
water

N  Param.: 9.45

sN Param.: 0.54
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
ammonia (in water)
H3N*
water

N  Param.: 9.48

sN Param.: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
N-phenylpropan-2-imine (in CH2Cl2)
C9H11N*
dichloromethane

N  Param.: 9.53

sN Param.: 0.85
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
imidazole (in water)
*
water

N  Param.: 9.63

sN Param.: 0.57
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)
C4H7NO*
dichloromethane

N  Param.: 9.81

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
(S)-2-(azidodiphenylmethyl)pyrrolidine
C17H18N4*
MeCN

N  Param.: 9.90

sN Param.: 1.22
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.02

sN Param.: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
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
theophylline anion (in water)
*
water

N  Param.: 10.06

sN Param.: 0.71
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
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
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
2,5-dimethyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.21

sN Param.: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
formohydrazide (in MeCN)
*
MeCN

N  Param.: 10.35

sN Param.: 0.76
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
1-methyl-benzimidazole (in MeCN)
*
MeCN

N  Param.: 10.37

sN Param.: 0.82
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
nicotine (in CH2Cl2)
C10H14N2*
dichloromethane

N  Param.: 10.40

sN Param.: 1.04
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
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
quinine
*
dichloromethane

N  Param.: 10.46

sN Param.: 0.75
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
tert-butylamine (in water)
C4H11N*
water

N  Param.: 10.48

sN Param.: 0.65
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.50

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
quinidine
*
dichloromethane

N  Param.: 10.54

sN Param.: 0.74
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
5-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.69

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
uracil anion (in water)
*
water

N  Param.: 10.75

sN Param.: 0.53
***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
saccharin anion (in MeCN)
*
MeCN

N  Param.: 10.78

sN Param.: 0.89
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
glycinenitrile (in water)
*
water

N  Param.: 10.80

sN Param.: 0.61
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
6-methoxy-quinoline (in MeCN)
*
MeCN

N  Param.: 10.86

sN Param.: 0.66
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
3-methylpyridine (in CH2Cl2)
C6H7N*
dichloromethane

N  Param.: 10.90

sN Param.: 0.93
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
adenine anion (in water)
*
water

N  Param.: 10.93

sN Param.: 0.62
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
5-methoxy-benzimidazole (in DMSO)
*
DMSO

N  Param.: 11.00

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

N  Param.: 11.00

sN Param.: 0.54
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
semicarbazide (in water)
CH5N3O*
water

N  Param.: 11.05

sN Param.: 0.52
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
pyridine (in H2O)
C5H5N*
water

N  Param.: 11.05

sN Param.: 0.73
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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
5,6-dimethyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 11.08

sN Param.: 0.71
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
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