O-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
91% ethanol/9% MeCN (v/v)   |
EtOH-MeCN mix | N Param.: 7.10 sN Param.: 0.90 |
 |
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
ethanol (in MeCN)  |
MeCN | N Param.: 7.13 sN Param.: 0.71 |
|
Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
80% methanol/20% MeCN (v/v)  |
MeOH-MeCN mix | N Param.: 7.20 sN Param.: 0.89 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
ethanol  |
EtOH | N Param.: 7.44 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
91% methanol/9% MeCN (v/v)  |
MeOH-MeCN mix | N Param.: 7.45 sN Param.: 0.87 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
methanol  |
MeOH | N Param.: 7.54 sN Param.: 0.92 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
OH- (in 50/50 water/MeCN)  |
water-MeCN mix | N Param.: 10.19 sN Param.: 0.62 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
OH- (in water)  |
water | N Param.: 10.47 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
DMSO (O attack)  |
DMSO | N Param.: 11.30 sN Param.: 0.74 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
benzoate (in 90AN10W)  |
aq MeCN | N Param.: 11.30 sN Param.: 0.72 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetate (in 80A20W)  |
aq acetone | N Param.: 12.50 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
2,2,2-trifluoroethanolate (in water)  |
water | N Param.: 12.66 sN Param.: 0.59 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
acetate (in 90A10W)  |
aq acetone | N Param.: 12.71 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
bromite (in water)  |
water | N Param.: 12.75 sN Param.: 0.59 |
|
Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
cumene peroxy anion (in H2O)  |
water | N Param.: 13.92 sN Param.: 0.61 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
beta-piperidinium-peroxypropionate  |
water | N Param.: 13.94 sN Param.: 0.62 |
|
Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
peroxy-beta-alanate  |
water | N Param.: 14.07 sN Param.: 0.56 |
|
Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
t-butylperoxy anion (in H2O)  |
water | N Param.: 14.29 sN Param.: 0.51 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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 |
p-nitrophenolate (in DMSO)  |
DMSO | N Param.: 14.32 sN Param.: 0.77 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
peroxy-GABA  |
water | N Param.: 14.33 sN Param.: 0.57 |
|
Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
peroxomonosulfate (in water)  |
water | N Param.: 14.41 sN Param.: 0.60 |
|
Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
hypochlorite (in water)  |
water | N Param.: 14.50 sN Param.: 0.58 |
|
Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
methanolate (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 14.51 sN Param.: 0.68 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
3,5-dinitrobenzoate (in MeCN)  |
MeCN | N Param.: 14.90 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
p-nitrophenolate (in DMF)  |
DMF | N Param.: 15.05 sN Param.: 0.80 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-nitrophenolate (in MeCN)  |
MeCN | N Param.: 15.14 sN Param.: 0.82 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-nitrobenzoate (in MeCN)  |
MeCN | N Param.: 15.30 sN Param.: 0.76 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
HOO- (in water)  |
water | N Param.: 15.40 sN Param.: 0.55 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
o-nitrophenolate (in DMSO)  |
DMSO | N Param.: 15.48 sN Param.: 0.71 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
2-phenylperoxyacetate (in H2O)  |
water | N Param.: 15.63 sN Param.: 0.56 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
methanolate (in methanol)  |
MeOH | N Param.: 15.78 sN Param.: 0.56 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
ethanolate (in ethanol)  |
EtOH | N Param.: 15.78 sN Param.: 0.65 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
o-nitrophenolate (in MeCN)  |
MeCN | N Param.: 15.83 sN Param.: 0.80 |
|
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phthalimidoperoxyhexanoate (in H2O)  |
water | N Param.: 16.02 sN Param.: 0.54 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
n-propanolate (in propan-1-ol)  |
nPrOH | N Param.: 16.03 sN Param.: 0.70 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
methyl carbonate (in MeCN)  |
MeCN | N Param.: 16.03 sN Param.: 0.64 |
|
Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414 |
ethanolate (in 91E9AN)  |
EtOH-MeCN mix | N Param.: 16.08 sN Param.: 0.62 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
benzoate (inMeCN)  |
MeCN | N Param.: 16.45 sN Param.: 0.72 |
|
J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998 |
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 |
hypobromite (in water)  |
water | N Param.: 16.69 sN Param.: 0.46 |
|
Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
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 |
benzoate (in MeCN)  |
MeCN | N Param.: 16.82 sN Param.: 0.70 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetate (in MeCN)  |
MeCN | N Param.: 16.90 sN Param.: 0.75 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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 |
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 91iPr9AN)  |
iPrOH-MeCN mix | N Param.: 17.71 sN Param.: 0.58 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
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 |
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 |