Mayr's Database of Reactivity Parameters

S-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
cysteine (dianionic, in water)
C3H5NO2S*
water

N  Param.: 23.43

sN Param.: 0.42
***Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
2-sulfidoacetate (in water)
C2H2O2S*
water

N  Param.: 22.62

sN Param.: 0.43
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)
C8H3F6S-*
DMSO

N  Param.: 19.71

sN Param.: 0.86
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
3-(trifluoromethyl)thiophenolate (in DMSO)
C7H4F3S-*
DMSO

N  Param.: 21.75

sN Param.: 0.86
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
3-chlorothiophenolate (in DMSO)
C6H4ClS-*
DMSO

N  Param.: 22.50

sN Param.: 0.78
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-(trifluoromethyl)thiophenolate (in DMSO)
C7H4F3S-*
DMSO

N  Param.: 21.30

sN Param.: 0.86
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-bromothiophenolate (in DMSO)
C6H4BrS-*
DMSO

N  Param.: 22.80

sN Param.: 0.78
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-methoxythiophenolate (in DMSO)
C7H7OS-*
DMSO

N  Param.: 24.97

sN Param.: 0.68
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)
*
MeCN

N  Param.: 23.61

sN Param.: 0.57
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
4-methylthiophenolate (in DMSO)
C7H7S-*
DMSO

N  Param.: 24.35

sN Param.: 0.69
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-nitrothiophenolate (in DMSO)
C6H4NO2S-*
DMSO

N  Param.: 18.92

sN Param.: 0.87
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
dimethylselenide (in CH2Cl2)
C2H6Se*
dichloromethane

N  Param.: 12.60

sN Param.: 0.72
-Chem. Eur. J. 2021, , AcceptArtic
10.1002/chem.202100977
dimethylsulfide (in CH2Cl2)
C2H6S*
dichloromethane

N  Param.: 12.32

sN Param.: 0.72
**Chem. Eur. J. 2021, , AcceptArtic
10.1002/chem.202100977
dimethylsulfide (in MeCN)
C2H6S*
MeCN

N  Param.: 12.70

sN Param.: 0.72
-Chem. Eur. J. 2021, , AcceptArtic
10.1002/chem.202100977
glutathione GSH(NH3+/S-)
*
water

N  Param.: 20.97

sN Param.: 0.56
***Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
morpholin-1-yl dithiocarbamate (in MeCN)
*
MeCN

N  Param.: 21.72

sN Param.: 0.64
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
N,N-dimethyl dithiocarbamate (in MeCN)
*
MeCN

N  Param.: 20.93

sN Param.: 0.69
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
naphthalene-2-thiolate (in DMSO)
 C10H7S-*
DMSO

N  Param.: 22.55

sN Param.: 0.83
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
O-ethyl dithiocarbonate (in MeCN)
*
MeCN

N  Param.: 19.30

sN Param.: 0.69
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
O-isopropyl dithiocarbonate (in MeCN)
*
MeCN

N  Param.: 18.27

sN Param.: 0.78
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
phenylsulfinate (in 50W50AN)
*
water-MeCN mix

N  Param.: 13.75

sN Param.: 0.68
***J. Am. Chem. Soc. 2010, 132, 4796-4805
10.1021/ja9102056
phenylsulfinate (in DMSO)
*
DMSO

N  Param.: 19.60

sN Param.: 0.60
***J. Am. Chem. Soc. 2010, 132, 4796-4805
10.1021/ja9102056
phenylsulfinate (in MeCN)
*
MeCN

N  Param.: 20.11

sN Param.: 0.59
***J. Am. Chem. Soc. 2010, 132, 4796-4805
10.1021/ja9102056
piperidin-1-yl dithiocarbamate (in MeCN)
*
MeCN

N  Param.: 23.84

sN Param.: 0.57
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
pyrrolidin-1-yl dithiocarbamate (in MeCN)
*
MeCN

N  Param.: 22.40

sN Param.: 0.63
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
SO3(2-) (in water)
O3S*
water

N  Param.: 16.83

sN Param.: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
thioacetate (in MeCN)
*
MeCN

N  Param.: 21.20

sN Param.: 0.63
***Org. Biomol. Chem. 2011, 9, 8046-8050
10.1039/c1ob06245j
thiocyanate (in MeCN)
CNS*
MeCN

N  Param.: 17.94

sN Param.: 0.60
***J. Am. Chem. Soc. 2003, 125, 14126-14132
10.1021/ja037317u
thiophenolate (in DMSO)
C6H5S-*
DMSO

N  Param.: 23.36

sN Param.: 0.74
***J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025