O-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
m-nitrophenolate (in MeCN)  |
MeCN | N Param.: 25.51 sN Param.: 0.43 |  | 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 |
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 DMSO) |
DMSO | N Param.: 22.62 sN Param.: 0.51 | | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
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-(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 |
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-(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 |
m-nitrophenolate (in DMSO) |
DMSO | N Param.: 21.29 sN Param.: 0.54 | | 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-methoxyphenolate (in MeCN) |
MeCN | N Param.: 20.62 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-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-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-(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 DMF) |
DMF | N Param.: 19.90 sN Param.: 0.82 | | 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 |
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 |
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-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-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-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-(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 |
phenolate (in DMF) |
DMF | N Param.: 18.86 sN Param.: 0.89 | | 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 |
3,5-dinitrobenzoate (in acetone) |
acetone | N Param.: 18.80 sN Param.: 0.62 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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-nitrobenzoate (in acetone) |
acetone | N Param.: 18.74 sN Param.: 0.68 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
peroxybenzoate (in H2O) |
water | N Param.: 18.57 sN Param.: 0.43 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
3-chloro-4-methoxyperoxybenzoate (in H2O) |
water | N Param.: 18.56 sN Param.: 0.48 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
phenolate (in MeCN) |
MeCN | N Param.: 18.53 sN Param.: 0.85 | | 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 |
magnesium 2-carboperoxybenzoate (in H2O) |
water | N Param.: 18.43 sN Param.: 0.46 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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 |
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 |
3-chloroperoxybenzoate (in H2O) |
water | N Param.: 18.19 sN Param.: 0.47 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
4-fluoroperoxybenzoate (in H2O) |
water | N Param.: 17.99 sN Param.: 0.47 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
3,5-dichloroperoxybenzoate (in H2O) |
water | N Param.: 17.93 sN Param.: 0.50 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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 |
4-methoxyperoxybenzoate (in H2O) |
water | N Param.: 17.84 sN Param.: 0.46 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
isopropanolate (in 91iPr9AN) |
iPrOH-MeCN mix | N Param.: 17.71 sN Param.: 0.58 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
4-nitroperoxybenzoate (in H2O) |
water | N Param.: 17.43 sN Param.: 0.50 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
isopropanolate (in propan-2-ol) |
iPrOH | N Param.: 17.03 sN Param.: 0.63 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
acetate (in MeCN) |
MeCN | N Param.: 16.90 sN Param.: 0.75 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
benzoate (in MeCN) |
MeCN | N Param.: 16.82 sN Param.: 0.70 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
n-propanolate (in 91nPr9AN) |
nPrOH-MeCN mix | N Param.: 16.73 sN Param.: 0.63 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF) |
THF | N Param.: 16.73 sN Param.: 0.63 | | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
hypobromite (in water) |
water | N Param.: 16.69 sN Param.: 0.46 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
o-nitrophenolate (in DMF) |
DMF | N Param.: 16.65 sN Param.: 0.70 | | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
benzoate (inMeCN) |
MeCN | N Param.: 16.45 sN Param.: 0.72 | | J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998 |