Mayr's Database of Reactivity Parameters

Nucleophiles

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

N  Param.: 10.80

sN Param.: 0.61
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethanolamine (in water)
C2H7NO *
water

N  Param.: 12.61

sN Param.: 0.58
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethylenediamine (in water)
C2H8N2 *
water

N  Param.: 13.28

sN Param.: 0.58
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
propargylamine (in water)
C3H5N *
water

N  Param.: 12.29

sN Param.: 0.59
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
allylamine (in water)
C3H7N *
water

N  Param.: 13.21

sN Param.: 0.54
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
benzylamine (in water)
C7H9N *
water

N  Param.: 13.44

sN Param.: 0.55
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
4-chloroaniline (in MeCN)
C6H6ClN *
MeCN

N  Param.: 12.92

sN Param.: 0.60
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
aniline (in water)
C6H7N *
water

N  Param.: 12.99

sN Param.: 0.73
*** 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
p-toluidine (in water)
C7H9N *
water

N  Param.: 13.00

sN Param.: 0.79
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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-methoxyaniline (in water)
C7H9NO *
water

N  Param.: 14.28

sN Param.: 0.68
*** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
4-methoxyaniline (in MeCN)
C7H9NO *
MeCN

N  Param.: 13.42

sN Param.: 0.73
*** 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
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
methyl glycinate (in water)
C3H7NO2 *
water

N  Param.: 12.08

sN Param.: 0.60
*** 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
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
anisole
C7H8O *
dichloromethane

N  Param.: -1.18

sN Param.: 1.20
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)
C8H5F3NO4S- *
DMSO

N  Param.: 14.49

sN Param.: 0.86
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)
C9H5F3NO2S- *
DMSO

N  Param.: 16.28

sN Param.: 0.75
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)
C9H5F6O2S- *
DMSO

N  Param.: 17.33

sN Param.: 0.74
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of benzyl trifluoromethyl sulfone (in DMSO)
C8H6F3O2S- *
DMSO

N  Param.: 18.67

sN Param.: 0.68
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO)
C9H8F3O2S- *
DMSO

N  Param.: 19.35

sN Param.: 0.67
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)
C8H5F3NO4S- *
MeOH-MeCN mix

N  Param.: 18.24

sN Param.: 0.66
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)
C9H5F3NO2S- *
MeOH-MeCN mix

N  Param.: 19.49

sN Param.: 0.63
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)
C9H5F6O2S- *
MeOH-MeCN mix

N  Param.: 20.72

sN Param.: 0.58
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
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
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
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
bis(4-nitrophenyl)methanide (in DMSO)
C13H9N2O4- *
DMSO

N  Param.: 19.92

sN Param.: 0.67
*** ARKIVOC 2008, (x), 37-53
10.3998/ark.5550190.[...]