Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
ethanolamine (in water)
C2H7NO *
water

N  Param.: 12.61

sN Param.: 0.58
*** 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
threonine (anionic, in water)
C4H8NO3 *
water

N  Param.: 12.69

sN Param.: 0.60
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
hydroxylamine (in MeCN)
*
MeCN

N  Param.: 12.80

sN Param.: 0.63
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
ethylamine (in water)
C2H7N *
water

N  Param.: 12.87

sN Param.: 0.58
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyridine (in CH2Cl2)
C5H5N *
dichloromethane

N  Param.: 12.90

sN Param.: 0.67
* Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
glycylglycine (anionic, in water)
C4H7N2O3 *
water

N  Param.: 12.91

sN Param.: 0.59
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
4-chloroaniline (in MeCN)
C6H6ClN *
MeCN

N  Param.: 12.92

sN Param.: 0.60
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C4H8N2 *
dichloromethane

N  Param.: 12.92

sN Param.: 0.77
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 12.95

sN Param.: 0.58
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
arginine (betaine, in water)
C6H14N4O2 *
water

N  Param.: 12.96

sN Param.: 0.57
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
3-bromo-4-(dimethylamino)pyridine (in MeCN)
*
MeCN

N  Param.: 12.96

sN Param.: 0.67
*** J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
*
dichloromethane

N  Param.: 12.98

sN Param.: 0.81
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
aniline (in water)
C6H7N *
water

N  Param.: 12.99

sN Param.: 0.73
*** 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
diethanolamine (in water)
C4H11NO2 *
water

N  Param.: 13.00

sN Param.: 0.61
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine
*
dichloromethane

N  Param.: 13.00

sN Param.: 0.83
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
alanine (anionic, in water)
C3H6NO2 *
water

N  Param.: 13.01

sN Param.: 0.58
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
O-HyperBTM (in CH2Cl2)
C19H20N2O *
dichloromethane

N  Param.: 13.01

sN Param.: 0.73
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
asparagine (anionic, in water)
C4H7N2O3 *
water

N  Param.: 13.03

sN Param.: 0.53
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
BTM (in CH2Cl2)
C15H12N2S *
dichloromethane

N  Param.: 13.06

sN Param.: 0.73
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C16H16N2 *
dichloromethane

N  Param.: 13.11

sN Param.: 0.83
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)
C5H9N *
dichloromethane

N  Param.: 13.12

sN Param.: 0.69
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
7-MeO-BTM (in CH2Cl2)
C16H14N2OS *
dichloromethane

N  Param.: 13.15

sN Param.: 0.75
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
serine (anionic, in water)
C3H6NO3 *
water

N  Param.: 13.16

sN Param.: 0.55
*** 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
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
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-(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
allylamine (in water)
C3H7N *
water

N  Param.: 13.21

sN Param.: 0.54
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
di(methoxyethyl)amine (in MeCN)
*
MeCN

N  Param.: 13.24

sN Param.: 0.93
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
4-acetamido-pyridine (in MeCN)
*
MeCN

N  Param.: 13.24

sN Param.: 0.67
*** J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
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
ethylenediamine (in water)
C2H8N2 *
water

N  Param.: 13.28

sN Param.: 0.58
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
O-DHPB (in CH2Cl2)
C10H10N2O *
dichloromethane

N  Param.: 13.31

sN Param.: 0.69
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
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
2-phenylethylamine (in water)
C8H11N *
water

N  Param.: 13.40

sN Param.: 0.57
*** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
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-methoxyaniline (in MeCN)
C7H9NO *
MeCN

N  Param.: 13.42

sN Param.: 0.73
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole
*
dichloromethane

N  Param.: 13.42

sN Param.: 0.73
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
HyperPTM
C27H24N2S *
dichloromethane

N  Param.: 13.43

sN Param.: 0.79
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
benzylamine (in water)
C7H9N *
water

N  Param.: 13.44

sN Param.: 0.55
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
glutamine (anionic, in water)
C5H9N2O3 *
water

N  Param.: 13.45

sN Param.: 0.54
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
HBTM (in CH2Cl2)
C16H14N2S *
dichloromethane

N  Param.: 13.45

sN Param.: 0.72
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
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
hydrazine (in water)
*
water

N  Param.: 13.46

sN Param.: 0.57
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
7-F-BTM (in CH2Cl2)
C15H11FN2S *
dichloromethane

N  Param.: 13.46

sN Param.: 0.66
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
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
9-MeS-HyperBTM
C20H22N2S2 *
dichloromethane

N  Param.: 13.49

sN Param.: 0.78
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
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
glycine (anionic, in water)
C2H4NO2 *
water

N  Param.: 13.51

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
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate
C13H22F3N3O3S *
MeCN

N  Param.: 13.57

sN Param.: 0.53
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
1,1,3,3-tetramethylguanidine
C5H13N3 *
dichloromethane

N  Param.: 13.58

sN Param.: 0.77
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
cyanate (in MeCN)
CNO- *
MeCN

N  Param.: 13.60

sN Param.: 0.84
*** Chem. Eur. J. 2008, 14, 3866-3868
10.1002/chem.200800314
pyridine (in MeCN)
C5H5N *
MeCN

N  Param.: 13.60

sN Param.: 0.60
*** Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
valine (anionic, in water)
C5H10NO2 *
water

N  Param.: 13.65

sN Param.: 0.57
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
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-methoxypyridine (in CH2Cl2)
C6H7NO *
dichloromethane

N  Param.: 13.70

sN Param.: 0.67
* Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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
isopropylamine (in MeCN)
*
MeCN

N  Param.: 13.77

sN Param.: 0.70
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
aspartate (dianionic, in water)
C4H5NO4 *
water

N  Param.: 13.81

sN Param.: 0.53
*** 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
methylamine (in water)
CH5N *
water

N  Param.: 13.85

sN Param.: 0.53
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
tetramisole (TM) (in CH2Cl2)
C11H12N2S *
dichloromethane

N  Param.: 13.86

sN Param.: 0.68
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
DHPB (in CH2Cl2)
C10H10N2S *
dichloromethane

N  Param.: 13.86

sN Param.: 0.78
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
glutamate (dianionic, in water)
C5H7NO4 *
water

N  Param.: 13.96

sN Param.: 0.54
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
2,2-dimethylpyrrolidine
C6H13N *
MeCN

N  Param.: 13.96

sN Param.: 0.76
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine
C12H17N3 *
dichloromethane

N  Param.: 14.00

sN Param.: 0.70
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-(triphenylsilyl)pyrrolidine
C22H23NSi *
MeCN

N  Param.: 14.00

sN Param.: 0.84
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
leucine (anionic, in water)
C6H12NO2 *
water

N  Param.: 14.01

sN Param.: 0.52
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
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
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine
*
dichloromethane

N  Param.: 14.10

sN Param.: 0.82
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
N-methylhydroxylamine (in MeCN)
*
MeCN

N  Param.: 14.10

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

N  Param.: 14.11

sN Param.: 0.71
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
phenylalanine (anionic, in water)
C9H10NO2 *
water

N  Param.: 14.12

sN Param.: 0.53
*** Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
2-Bz super-dmap (in MeCN)
*
MeCN

N  Param.: 14.19

sN Param.: 0.67
*** Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
Se-HyperBTM (in THF)
C19H20N2Se *
THF

N  Param.: 14.19

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-BTM (in CH2Cl2)
C15H12N2Se *
dichloromethane

N  Param.: 14.27

sN Param.: 0.63
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
4-methoxyaniline (in water)
C7H9NO *
water

N  Param.: 14.28

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

N  Param.: 14.29

sN Param.: 0.67
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
2-benzyl-1,1,3,3-tetramethylguanidine
C12H19N3 *
dichloromethane

N  Param.: 14.36

sN Param.: 0.79
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
allylamine (in MeCN)
*
MeCN

N  Param.: 14.37

sN Param.: 0.66
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
2-aminobutan-1-ol (in DMSO)
*
DMSO

N  Param.: 14.39

sN Param.: 0.67
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
Se-HBTM (in CH2Cl2)
C16H14N2Se *
dichloromethane

N  Param.: 14.42

sN Param.: 0.67
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
C8H15N3 *
dichloromethane

N  Param.: 14.43

sN Param.: 0.81
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)
C5H10N2 *
MeCN

N  Param.: 14.43

sN Param.: 0.79
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)
C5H9N3 *
dichloromethane

N  Param.: 14.44

sN Param.: 0.79
*** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)
*
dichloromethane

N  Param.: 14.45

sN Param.: 0.78
*** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
HyperNTM
C23H22N2S *
dichloromethane

N  Param.: 14.47

sN Param.: 0.72
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-PivO-HyperBTM
C24H28N2O2S *
dichloromethane

N  Param.: 14.49

sN Param.: 0.66
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
dipropylamine (in MeCN)
*
MeCN

N  Param.: 14.51

sN Param.: 0.80
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine
C22H21FN2 *
dichloromethane

N  Param.: 14.57

sN Param.: 0.75
*** Eur. J. Org. Chem. 2014, , 1202-1211
10.1002/ejoc.201301730
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)
C5H10N2 *
DMSO

N  Param.: 14.58

sN Param.: 0.79
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
4-(morpholino)pyridine (in CH2Cl2)
C9H12N2O *
dichloromethane

N  Param.: 14.59

sN Param.: 0.69
*** Eur. J. Org. Chem. 2016, , 4050-4058
10.1002/ejoc.201600572
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C10H12N2 *
dichloromethane

N  Param.: 14.62

sN Param.: 0.72
*** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
Te-BTM (in CH2Cl2)
C15H12N2Te *
dichloromethane

N  Param.: 14.62

sN Param.: 0.66
*** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865