Mayr's Database of Reactivity Parameters

N-Nucleophiles

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

N  Param.: 23.05

sN Param.: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.67

sN Param.: 0.54
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 22.41

sN Param.: 0.45
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.40

sN Param.: 0.59
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.29

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.09

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.03

sN Param.: 0.50
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2,4-dimethyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 20.69

sN Param.: 0.60
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
N-methyl-pyrrolidine (in CH2Cl2)
*
dichloromethane

N  Param.: 20.60

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
N-methyl-pyrrolidine (in MeCN)
*
MeCN

N  Param.: 20.59

sN Param.: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
quinuclidine (in MeCN)
C7H13N*
MeCN

N  Param.: 20.54

sN Param.: 0.60
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
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
cyanamide anion (in DMSO)
*
DMSO

N  Param.: 20.33

sN Param.: 0.64
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4-pyridone anion (in MeCN)
*
MeCN

N  Param.: 20.22

sN Param.: 0.49
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
2-pyridone anion (in MeCN)
*
MeCN

N  Param.: 20.11

sN Param.: 0.57
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
prolinate (in MeCN)
C5H8NO2-*
MeCN

N  Param.: 19.95

sN Param.: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-pyridone anion (in DMSO)
*
DMSO

N  Param.: 19.91

sN Param.: 0.60
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2*
dichloromethane

N  Param.: 19.31

sN Param.: 0.46
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
benzimidazole anion (in DMSO)
*
DMSO

N  Param.: 19.13

sN Param.: 0.55
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-pyridone anion (in DMSO)
*
DMSO

N  Param.: 18.97

sN Param.: 0.62
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
N-methyl-piperidine (in CH2Cl2)
*
dichloromethane

N  Param.: 18.90

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
DABCO (in MeCN)
C6H12N2*
MeCN

N  Param.: 18.80

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
N-methyl-piperidine (in MeCN)
*
MeCN

N  Param.: 18.72

sN Param.: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
methanesulfonamide anion (in DMSO)
*
DMSO

N  Param.: 18.61

sN Param.: 0.53
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
pyrrolidine (inMeCN)
C4H9N*
MeCN

N  Param.: 18.58

sN Param.: 0.61
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine
C9H18N2*
MeCN

N  Param.: 18.33

sN Param.: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
perhydroazepine (in water)
C6H13N*
water

N  Param.: 18.29

sN Param.: 0.46
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
piperidine (in water)
C5H11N*
water

N  Param.: 18.13

sN Param.: 0.44
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
proline (anionic, in water)
C5H8NO2*
water

N  Param.: 18.08

sN Param.: 0.50
***Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
adenine anion (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.55
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
dimethylamine (in MeCN)
*
MeCN

N  Param.: 17.96

sN Param.: 0.63
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 17.90

sN Param.: 0.48
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
trimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 17.75

sN Param.: 0.53
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
methylhydrazine (in MeCN)
*
MeCN

N  Param.: 17.73

sN Param.: 0.58
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
2-Bn super-dmap (in MeCN)
*
MeCN

N  Param.: 17.69

sN Param.: 0.57
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
thymine anion (in DMSO)
*
DMSO

N  Param.: 17.63

sN Param.: 0.62
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
(S)-N,N-dimethylpyrrolidine-2-carboxamide
C7H14N2O*
MeCN

N  Param.: 17.61

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
4,4-dimethyl-glutarimide anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.63
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
hydantoin anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.55
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
C14H15F6N3O*
MeCN

N  Param.: 17.50

sN Param.: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-benzylpyrrolidine
C11H15N*
MeCN

N  Param.: 17.43

sN Param.: 0.66
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
C7H16N2*
MeCN

N  Param.: 17.41

sN Param.: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
piperidine (in MeCN)
*
MeCN

N  Param.: 17.35

sN Param.: 0.68
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
triethylamine (in CH2Cl2)
*
dichloromethane

N  Param.: 17.30

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
(S)-pyrrolidin-2-ylmethanamine
C5H12N2*
MeCN

N  Param.: 17.24

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methylhydrazine (in water)
*
water

N  Param.: 17.23

sN Param.: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
piperazine (in water)
C4H10N2*
water

N  Param.: 17.22

sN Param.: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyrrolidine (in water)
C4H9N*
water

N  Param.: 17.21

sN Param.: 0.49
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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