O-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
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 |
10% water/90% acetone (v/v) |
water-acetone mix | N Param.: 5.70 sN Param.: 0.85 | | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
20% water/80% acetone (v/v) |
water-acetone mix | N Param.: 5.77 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
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 |
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 |
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 |
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 |
33% water/67% MeCN (v/v) |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80% MeCN (v/v) |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% water/90% MeCN (v/v) |
water-MeCN mix | N Param.: 4.56 sN Param.: 0.94 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% water/90%TFE (v/v) |
water-TFE mix | N Param.: 2.93 sN Param.: 0.88 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%TFE (v/v) |
water-TFE mix | N Param.: 3.20 sN Param.: 0.88 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
40% water/60%TFE (v/v) |
water-TFE mix | N Param.: 3.42 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 |
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 |
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 |
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 |
methanol |
MeOH | N Param.: 7.54 sN Param.: 0.92 | | 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 |
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 |
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 |
40% water/60%EtOH (v/v) |
water-EtOH mix | N Param.: 6.28 sN Param.: 0.87 | | 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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
33% ethanol/67% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 6.06 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% ethanol/80% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 5.77 sN Param.: 0.92 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% ethanol/90% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 5.19 sN Param.: 0.96 | | 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 |
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 |
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 |
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 |
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 |
20% methanol/80% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 6.04 sN Param.: 0.94 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% methanol/90% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 5.55 sN Param.: 0.97 | | 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 |
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 |
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 |
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 |
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 |
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 |
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 91nPr9AN) |
nPrOH-MeCN mix | N Param.: 16.73 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 |
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 |
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 |
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-nitrobenzoate (in acetone) |
acetone | N Param.: 18.74 sN Param.: 0.68 | | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
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 |
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 |
DMSO (O attack) |
DMSO | N Param.: 11.30 sN Param.: 0.74 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
methyl carbonate (in MeCN) |
MeCN | N Param.: 16.03 sN Param.: 0.64 | | Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414 |
trifluoroethanol |
TFE | N Param.: 1.11 sN Param.: 0.96 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
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 |
30% water/70% HFIP (w/w) |
water-HFIP mix | N Param.: 1.65 sN Param.: 0.96 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
10% water/90% HFIP (w/w) |
water-HFIP mix | N Param.: 0.96 sN Param.: 0.93 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
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 |
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 |
3% water/97% HFIP (w/w) |
water-HFIP mix | N Param.: -1.19 sN Param.: 1.08 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
2% water/98% HFIP (w/w) |
water-HFIP mix | N Param.: -1.62 sN Param.: 1.10 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
1% water/99% HFIP (w/w) |
water-HFIP mix | N Param.: -1.93 sN Param.: 1.09 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
(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 |
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 |
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 |
phthalimidoperoxyhexanoate (in H2O) |
water | N Param.: 16.02 sN Param.: 0.54 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
peroxybenzoate (in H2O) |
water | N Param.: 18.57 sN Param.: 0.43 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
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.[...] |
bromite (in water) |
water | N Param.: 12.75 sN Param.: 0.59 | | 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.[...] |
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 |
peroxy-GABA |
water | N Param.: 14.33 sN Param.: 0.57 | | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 |
methanol (in MeCN) |
MeCN | N Param.: 6.86 sN Param.: 0.73 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
ethanol (in MeCN) |
MeCN | N Param.: 7.13 sN Param.: 0.71 | | 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 |
tert-butanol (in MeCN) |
MeCN | N Param.: 5.35 sN Param.: 0.72 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
water (in MeCN) |
MeCN | N Param.: 5.79 sN Param.: 0.72 | | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
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 |