S- and Se-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
SO3(2-) (in water)  |
water | N Param.: 16.83 sN Param.: 0.56 |  | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2-sulfidoacetate (in water) |
water | N Param.: 22.62 sN Param.: 0.43 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
thiocyanate (in MeCN) |
MeCN | N Param.: 17.94 sN Param.: 0.60 | | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
cysteine (dianionic, in water) |
water | N Param.: 23.43 sN Param.: 0.42 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
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 |
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 |
thioacetate (in MeCN) |
MeCN | N Param.: 21.20 sN Param.: 0.63 | | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
dimethylsulfide (in CH2Cl2) |
dichloromethane | N Param.: 12.32 sN Param.: 0.72 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dimethylsulfide (in MeCN) |
MeCN | N Param.: 12.70 sN Param.: 0.72 |  | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dimethylselenide (in CH2Cl2) |
dichloromethane | N Param.: 12.60 sN Param.: 0.72 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dibutylsulfide (in CH2Cl2) |
dichloromethane | N Param.: 11.86 sN Param.: 0.74 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiophene (in CH2Cl2) |
dichloromethane | N Param.: 13.10 sN Param.: 0.72 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiophene (in MeCN) |
MeCN | N Param.: 13.30 sN Param.: 0.72 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiopyran (in CH2Cl2) |
dichloromethane | N Param.: 11.94 sN Param.: 0.75 | | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
4-nitrothiophenolate (in DMSO) |
DMSO | N Param.: 18.92 sN Param.: 0.87 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3,5-bis(trifluoromethyl)thiophenolate (in DMSO) |
DMSO | N Param.: 19.71 sN Param.: 0.86 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-(trifluoromethyl)thiophenolate (in DMSO) |
DMSO | N Param.: 21.30 sN Param.: 0.86 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-(trifluoromethyl)thiophenolate (in DMSO) |
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) |
DMSO | N Param.: 22.50 sN Param.: 0.78 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-bromothiophenolate (in DMSO) |
DMSO | N Param.: 22.80 sN Param.: 0.78 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
thiophenolate (in DMSO) |
DMSO | N Param.: 23.36 sN Param.: 0.74 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-methylthiophenolate (in DMSO) |
DMSO | N Param.: 24.35 sN Param.: 0.69 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
naphthalene-2-thiolate (in DMSO) |
DMSO | N Param.: 22.55 sN Param.: 0.83 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-methoxythiophenolate (in DMSO) |
DMSO | N Param.: 24.97 sN Param.: 0.68 | | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |