Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
m-nitrophenolate (in DMF)   |
DMF | N Param.: 22.41 sN Param.: 0.54 |
 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-cyanophenolate (in DMSO)  |
DMSO | N Param.: 18.78 sN Param.: 0.57 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-cyanophenolate (in MeCN)  |
MeCN | N Param.: 19.58 sN Param.: 0.59 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-cyanophenolate (in DMF)  |
DMF | N Param.: 17.85 sN Param.: 0.71 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
o-(trifluoromethyl)phenolate (in DMSO)  |
DMSO | N Param.: 18.47 sN Param.: 0.61 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
o-(trifluoromethyl)phenolate (in MeCN)  |
MeCN | N Param.: 18.39 sN Param.: 0.69 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
o-(trifluoromethyl)phenolate (in DMF)  |
DMF | N Param.: 20.37 sN Param.: 0.58 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(trifluoromethyl)phenolate (in DMSO)  |
DMSO | N Param.: 18.98 sN Param.: 0.63 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(trifluoromethyl)phenolate (in MeCN)  |
MeCN | N Param.: 21.69 sN Param.: 0.53 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(trifluoromethyl)phenolate (in DMF)  |
DMF | N Param.: 22.05 sN Param.: 0.53 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
m-(trifluoromethyl)phenolate (in DMSO)  |
DMSO | N Param.: 22.62 sN Param.: 0.51 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
m-(trifluoromethyl)phenolate (in MeCN)  |
MeCN | N Param.: 23.20 sN Param.: 0.51 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
m-(trifluoromethyl)phenolate (in DMF)  |
DMF | N Param.: 23.40 sN Param.: 0.51 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-chlorophenolate (in DMSO)  |
DMSO | N Param.: 20.34 sN Param.: 0.64 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-chlorophenolate (in MeCN)  |
MeCN | N Param.: 18.32 sN Param.: 0.82 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-chlorophenolate (in DMF)  |
DMF | N Param.: 19.67 sN Param.: 0.72 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in DMSO)  |
DMSO | N Param.: 19.86 sN Param.: 0.71 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in MeCN)  |
MeCN | N Param.: 18.53 sN Param.: 0.85 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in DMF)  |
DMF | N Param.: 18.86 sN Param.: 0.89 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methylphenolate (in DMSO)  |
DMSO | N Param.: 19.08 sN Param.: 0.87 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methylphenolate (in DMF)  |
DMF | N Param.: 19.65 sN Param.: 0.85 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(tert-butyl)phenolate (in DMSO)  |
DMSO | N Param.: 19.67 sN Param.: 0.79 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(tert-butyl)phenolate (in MeCN)  |
MeCN | N Param.: 21.70 sN Param.: 0.58 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(tert-butyl)phenolate (in DMF)  |
DMF | N Param.: 19.90 sN Param.: 0.80 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methoxyphenolate (in DMSO)  |
DMSO | N Param.: 20.09 sN Param.: 0.80 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methoxyphenolate (in MeCN)  |
MeCN | N Param.: 20.62 sN Param.: 0.69 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methoxyphenolate (in DMF)  |
DMF | N Param.: 19.90 sN Param.: 0.82 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
m-methoxyphenolate (in MeCN)  |
MeCN | N Param.: 18.81 sN Param.: 0.80 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
o,o'-di-tert-butylphenolate (in DMSO)  |
DMSO | N Param.: 21.02 sN Param.: 0.59 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-methylphenolate (in H2O)  |
water | N Param.: 14.30 sN Param.: 0.55 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
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 |
prolinate (in MeCN)  |
MeCN | N Param.: 19.95 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyrrolidine (in MeCN)  |
MeCN | N Param.: 16.78 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (inMeCN)  |
MeCN | N Param.: 18.58 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-isopropylpyrrolidine  |
MeCN | N Param.: 16.44 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2-dimethylpyrrolidine  |
MeCN | N Param.: 13.96 sN Param.: 0.76 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine  |
MeCN | N Param.: 17.43 sN Param.: 0.66 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-benzhydrylpyrrolidine  |
MeCN | N Param.: 16.61 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanamine  |
MeCN | N Param.: 17.24 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine  |
MeCN | N Param.: 17.41 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine  |
MeCN | N Param.: 18.33 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(azidomethyl)pyrrolidine  |
MeCN | N Param.: 15.43 sN Param.: 0.73 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanol  |
MeCN | N Param.: 16.74 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(methoxymethyl)pyrrolidine  |
MeCN | N Param.: 16.50 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(trifluoromethyl)pyrrolidine  |
MeCN | N Param.: 11.34 sN Param.: 0.73 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methyl L-prolinate  |
MeCN | N Param.: 14.75 sN Param.: 0.82 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethylpyrrolidine-2-carboxamide  |
MeCN | N Param.: 17.61 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N-propylpyrrolidine-2-carboxamide  |
MeCN | N Param.: 15.20 sN Param.: 0.73 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione  |
MeCN | N Param.: 15.90 sN Param.: 0.77 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole  |
MeCN | N Param.: 15.32 sN Param.: 0.72 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |