O-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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.[...] |
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 |
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-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 |
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 |
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 |
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 |
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 |
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-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-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-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-cyanophenolate (in DMF) |
DMF | N Param.: 17.85 sN Param.: 0.71 | | 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 |
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 |
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-(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 |
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 |
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 |
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 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 DMF) |
DMF | N Param.: 23.40 sN Param.: 0.51 | | 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-chlorophenolate (in MeCN) |
MeCN | N Param.: 18.32 sN Param.: 0.82 | | 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 |
phenolate (in DMSO) |
DMSO | N Param.: 19.86 sN Param.: 0.71 | | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in MeCN) |
MeCN | N Param.: 18.53 sN Param.: 0.85 | | 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 |
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-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-(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-(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-(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 DMSO) |
DMSO | N Param.: 20.09 sN Param.: 0.80 | | 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 |
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 |
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 |
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-methylphenolate (in H2O) |
water | N Param.: 14.30 sN Param.: 0.55 | | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
H2O (in water) |
water | N Param.: 5.20 sN Param.: 0.89 | | 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 |
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 |
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 |
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 |
trifluoroethanol |
TFE | N Param.: 1.11 sN Param.: 0.96 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
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 |
DMSO (O attack) |
DMSO | N Param.: 11.30 sN Param.: 0.74 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
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 |