O-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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-(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 |
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 |
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 |
isopropanol (in MeCN) |
MeCN | N Param.: 6.82 sN Param.: 0.70 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
hypochlorite (in water) |
water | N Param.: 14.50 sN Param.: 0.58 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
hypobromite (in water) |
water | N Param.: 16.69 sN Param.: 0.46 | | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] |
HOO- (in water) |
water | N Param.: 15.40 sN Param.: 0.55 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
H2O (in water) |
water | N Param.: 5.20 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
ethanolate (in ethanol) |
EtOH | N Param.: 15.78 sN Param.: 0.65 | | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
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 |
ethanol (in MeCN) |
MeCN | N Param.: 7.13 sN Param.: 0.71 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
ethanol |
EtOH | N Param.: 7.44 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
DMSO (O attack) |
DMSO | N Param.: 11.30 sN Param.: 0.74 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
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.[...] |
beta-piperidinium-peroxypropionate |
water | N Param.: 13.94 sN Param.: 0.62 | | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
benzoate (inMeCN) |
MeCN | N Param.: 16.45 sN Param.: 0.72 | | J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998 |
benzoate (in MeCN) |
MeCN | N Param.: 16.82 sN Param.: 0.70 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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 MeCN) |
MeCN | N Param.: 16.90 sN Param.: 0.75 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetate (in 90A10W) |
aq acetone | N Param.: 12.71 sN Param.: 0.68 | | 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 |
91% water/9% MeCN (v/v) |
water-MeCN mix | N Param.: 5.16 sN Param.: 0.91 | | 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 |
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 |
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 |
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 |
90% water/10%TFE (v/v) |
water-TFE mix | N Param.: 5.04 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
90% water/10%EtOH (v/v) |
water-EtOH mix | N Param.: 5.38 sN Param.: 0.91 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%TFE (v/v) |
water-TFE mix | N Param.: 4.78 sN Param.: 0.83 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%EtOH (v/v) |
water-EtOH mix | N Param.: 5.54 sN Param.: 0.94 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20% MeCN (v/v) |
water-MeCN mix | N Param.: 5.04 sN Param.: 0.89 | | 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 |
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 |
7% water/93% HFIP (w/w) |
water-HFIP mix | N Param.: 0.34 sN Param.: 0.96 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
67% water/33% MeCN (v/v) |
water-MeCN mix | N Param.: 5.05 sN Param.: 0.90 | | 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 |
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 |
60% water/40%TFE (v/v) |
water-TFE mix | N Param.: 3.77 sN Param.: 0.88 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
60% water/40%EtOH (v/v) |
water-EtOH mix | N Param.: 5.81 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50%TFE (v/v) |
water-TFE mix | N Param.: 3.57 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50%EtOH (v/v) |
water-EtOH mix | N Param.: 5.96 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50% MeCN (v/v) |
water-MeCN mix | N Param.: 5.05 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50% HFIP (w/w) |
water-HFIP mix | N Param.: 1.50 sN Param.: 1.03 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
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 |
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 |
5% water/95% HFIP (w/w) |
water-HFIP mix | N Param.: -0.10 sN Param.: 0.97 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |