Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
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
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
N-(phenylmethyl)propan-2-imine (in CH2Cl2)
C10H13N*
dichloromethane

N  Param.: 11.13

sN Param.: 0.73
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
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-Me super-dmap (in MeCN)
*
MeCN

N  Param.: 16.65

sN Param.: 0.58
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Et super-dmap (in MeCN)
*
MeCN

N  Param.: 16.81

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Bn super-dmap (in MeCN)
*
MeCN

N  Param.: 17.69

sN Param.: 0.57
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Ac super-dmap (in MeCN)
*
MeCN

N  Param.: 15.39

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Bz super-dmap (in MeCN)
*
MeCN

N  Param.: 14.19

sN Param.: 0.67
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
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 MeCN)
*
MeCN

N  Param.: 11.47

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

N  Param.: 11.58

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

N  Param.: 11.90

sN Param.: 0.73
***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
1-phenyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.31

sN Param.: 0.67
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.74

sN Param.: 0.76
***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
4-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.79

sN Param.: 0.77
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2,4-dimethyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.51

sN Param.: 0.84
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-(trimethylsilyl)-imidazole (in MeCN)
*
MeCN

N  Param.: 11.43

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

N  Param.: 10.50

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-benzimidazole (in MeCN)
*
MeCN

N  Param.: 10.37

sN Param.: 0.82
***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
5-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.69

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
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
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
5-methoxy-benzimidazole (in DMSO)
*
DMSO

N  Param.: 11.00

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