Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
4-amino-3,5-dibromo-pyridine (in MeCN)
*
MeCN

N  Param.: 11.11

sN Param.: 0.75
*** J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
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
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-phenyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.31

sN Param.: 0.67
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-(trifluoromethyl)pyrrolidine
C5H8F3N *
MeCN

N  Param.: 11.34

sN Param.: 0.73
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
ammonia (in MeCN)
*
MeCN

N  Param.: 11.39

sN Param.: 0.69
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
tert-butyl hydrazinecarboxylate (in MeCN)
*
MeCN

N  Param.: 11.40

sN Param.: 0.70
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
hydroxylamine (in water)
H3NO *
water

N  Param.: 11.41

sN Param.: 0.55
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
1-(trimethylsilyl)-imidazole (in MeCN)
*
MeCN

N  Param.: 11.43

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

N  Param.: 11.47

sN Param.: 0.79
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
3-methylpyridine (in MeCN)
C6H7N *
MeCN

N  Param.: 11.50

sN Param.: 0.80
*** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
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
benzotriazole anion (in water)
*
water

N  Param.: 11.52

sN Param.: 0.67
*** Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
imidazole (in DMSO)
*
DMSO

N  Param.: 11.58

sN Param.: 0.79
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
4-methyl-quinoline alias lepidine (in MeCN)
*
MeCN

N  Param.: 11.60

sN Param.: 0.62
*** J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
nicotine (in MeCN)
C10H14N2 *
MeCN

N  Param.: 11.60

sN Param.: 0.81
*** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
guanine anion (in water)
*
water

N  Param.: 11.63

sN Param.: 0.59
*** Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 11.72

sN Param.: 0.73
*** Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
2-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.74

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

N  Param.: 11.90

sN Param.: 0.73
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
isopropylamine (in water)
C3H9N *
water

N  Param.: 12.00

sN Param.: 0.56
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine
C20H27NOSi *
MeCN

N  Param.: 12.03

sN Param.: 0.98
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methyl glycinate (in water)
C3H7NO2 *
water

N  Param.: 12.08

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

N  Param.: 12.09

sN Param.: 0.52
*** Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
thiocyanate (in MeCN)
CNS *
MeCN

N  Param.: 12.13

sN Param.: 0.60
* J. Am. Chem. Soc. 2003, 125, 14126-14132
10.1021/ja037317u
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
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
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
glycylglycylglycine (anionic, in water)
C6H10N3O4 *
water

N  Param.: 12.26

sN Param.: 0.63
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
propargylamine (in water)
C3H5N *
water

N  Param.: 12.29

sN Param.: 0.59
*** 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
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C9H10N2 *
dichloromethane

N  Param.: 12.31

sN Param.: 0.77
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
tert-butylamine (in MeCN)
*
MeCN

N  Param.: 12.35

sN Param.: 0.72
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
trimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 12.43

sN Param.: 0.75
*** Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,3-dimethylimidazolidin-2-imine
C5H11N3 *
dichloromethane

N  Param.: 12.46

sN Param.: 0.87
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
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
benzohydrazide (in MeCN)
*
MeCN

N  Param.: 12.49

sN Param.: 0.66
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
7-Ms-HyperBTM
C20H22N2O2S2 *
dichloromethane

N  Param.: 12.52

sN Param.: 0.75
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434