O-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
phthalimidoperoxyhexanoate (in H2O) |
water | N Param.: 16.02 sN Param.: 0.54 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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 |
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 |
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 |
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 |
HOO- (in water) |
water | N Param.: 15.40 sN Param.: 0.55 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
p-nitrobenzoate (in MeCN) |
MeCN | N Param.: 15.30 sN Param.: 0.76 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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-nitrophenolate (in DMF) |
DMF | N Param.: 15.05 sN Param.: 0.80 | | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
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 |
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 |
hypochlorite (in water) |
water | N Param.: 14.50 sN Param.: 0.58 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
peroxomonosulfate (in water) |
water | N Param.: 14.41 sN Param.: 0.60 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
peroxy-GABA |
water | N Param.: 14.33 sN Param.: 0.57 | | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
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 |
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 |
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 |
peroxy-beta-alanate |
water | N Param.: 14.07 sN Param.: 0.56 | | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
beta-piperidinium-peroxypropionate |
water | N Param.: 13.94 sN Param.: 0.62 | | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
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 |
bromite (in water) |
water | N Param.: 12.75 sN Param.: 0.59 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
acetate (in 90A10W) |
aq acetone | N Param.: 12.71 sN Param.: 0.68 | | 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 80A20W) |
aq acetone | N Param.: 12.50 sN Param.: 0.60 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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 |
OH- (in water) |
water | N Param.: 10.47 sN Param.: 0.61 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
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 |
methanol |
MeOH | N Param.: 7.54 sN Param.: 0.92 | | 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 |
ethanol |
EtOH | N Param.: 7.44 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
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 (in MeCN) |
MeCN | N Param.: 7.13 sN Param.: 0.71 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
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 |
91% n-propanol/9% MeCN (v/v) |
nPrOH-MeCN mix | N Param.: 7.05 sN Param.: 0.80 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
10% water/90%EtOH (v/v) |
water-EtOH mix | N Param.: 7.03 sN Param.: 0.86 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
67% methanol/33% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 7.01 sN Param.: 0.91 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% ethanol/20% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 6.94 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
methanol (in MeCN) |
MeCN | N Param.: 6.86 sN Param.: 0.73 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
isopropanol (in MeCN) |
MeCN | N Param.: 6.82 sN Param.: 0.70 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
67% ethanol/33% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 6.74 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%EtOH (v/v) |
water-EtOH mix | N Param.: 6.68 sN Param.: 0.85 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% methanol/50% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 6.67 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
91% propan-2-ol/9% MeCN (v/v) |
iPrOH-MeCN mix | N Param.: 6.49 sN Param.: 0.96 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
33% methanol/67% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 6.38 sN Param.: 0.92 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% ethanol/50% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |