Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)   |
DMSO | N Param.: 24.88 sN Param.: 0.49 |
 |
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)  |
DMSO | N Param.: 26.90 sN Param.: 0.45 |
|
J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)  |
DMSO | N Param.: 15.85 sN Param.: 1.04 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 2-phenylmalononitrile (in DMSO)  |
DMSO | N Param.: 15.58 sN Param.: 1.00 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)  |
DMSO | N Param.: 15.97 sN Param.: 0.72 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)  |
DMSO | N Param.: 15.07 sN Param.: 0.79 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)  |
DMSO | N Param.: 14.99 sN Param.: 0.83 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
barbiturate anion (in DMSO)  |
DMSO | N Param.: 15.59 sN Param.: 0.80 |
|
J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
1,3-dimethylbarbiturate anion (in DMSO)  |
DMSO | N Param.: 17.46 sN Param.: 0.72 |
|
J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
2-thiobarbiturate anion (in DMSO)  |
DMSO | N Param.: 14.24 sN Param.: 0.82 |
|
J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
1,3-diethyl-thiobarbiturate anion (in DMSO)  |
DMSO | N Param.: 14.90 sN Param.: 0.80 |
|
J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)  |
DMSO | N Param.: 26.95 sN Param.: 0.52 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)  |
DMSO | N Param.: 27.77 sN Param.: 0.47 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)  |
DMSO | N Param.: 29.10 sN Param.: 0.50 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)  |
DMSO | N Param.: 29.02 sN Param.: 0.49 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)  |
DMSO | N Param.: 30.82 sN Param.: 0.41 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
cyano((diphenylmethylene)amino)methanide  |
DMSO | N Param.: 29.50 sN Param.: 0.50 |
|
Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)  |
DMSO | N Param.: 16.26 sN Param.: 0.83 |
|
J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
phenolate (in DMSO)  |
DMSO | N Param.: 19.86 sN Param.: 0.71 |
|
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-(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-methoxyphenolate (in DMSO)  |
DMSO | N Param.: 20.09 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 |
4-nitrothiophenolate (in DMSO)  |
DMSO | N Param.: 18.92 sN Param.: 0.87 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)  |
DMSO | N Param.: 19.71 sN Param.: 0.86 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-(trifluoromethyl)thiophenolate (in DMSO)  |
DMSO | N Param.: 21.30 sN Param.: 0.86 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-(trifluoromethyl)thiophenolate (in DMSO)  |
DMSO | N Param.: 21.75 sN Param.: 0.86 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-chlorothiophenolate (in DMSO)  |
DMSO | N Param.: 22.50 sN Param.: 0.78 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-bromothiophenolate (in DMSO)  |
DMSO | N Param.: 22.80 sN Param.: 0.78 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
thiophenolate (in DMSO)  |
DMSO | N Param.: 23.36 sN Param.: 0.74 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-methylthiophenolate (in DMSO)  |
DMSO | N Param.: 24.35 sN Param.: 0.69 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
naphthalene-2-thiolate (in DMSO)  |
DMSO | N Param.: 22.55 sN Param.: 0.83 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-methoxythiophenolate (in DMSO)  |
DMSO | N Param.: 24.97 sN Param.: 0.68 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)  |
DMSO | N Param.: 21.16 sN Param.: 0.59 |
|
Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)  |
DMSO | N Param.: 19.91 sN Param.: 0.62 |
|
Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)  |
DMSO | N Param.: 20.76 sN Param.: 0.60 |
|
Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)  |
DMSO | N Param.: 19.41 sN Param.: 0.61 |
|
Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)  |
DMSO | N Param.: 19.36 sN Param.: 0.68 |
|
Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
enolate of 3-isochromanone (in DMSO)  |
DMSO | N Param.: 25.39 sN Param.: 0.54 |
|
J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
enolate of 2-coumaranone (in DMSO)  |
DMSO | N Param.: 19.60 sN Param.: 0.75 |
|
J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
ethanol  |
EtOH | N Param.: 7.44 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
chloride (in EtOH)  |
EtOH | N Param.: 14.70 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
ethanolate (in ethanol)  |
EtOH | N Param.: 15.78 sN Param.: 0.65 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
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 |
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 |
azide ion (in 91E9AN)  |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 |
|
J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
chloride (in hexafluoroisopropanol)  |
HFIP | N Param.: 8.00 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
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 |
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 |
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 |
azide ion (in 91iPr9AN)  |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 |
|
J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
cyanide (in MeCN)  |
MeCN | N Param.: 16.27 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 |
thiocyanate (in MeCN)  |
MeCN | N Param.: 17.94 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
thiocyanate (in MeCN)  |
MeCN | N Param.: 12.13 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
chloride (in MeCN)  |
MeCN | N Param.: 17.20 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
nitrite ion (in MeCN)  |
MeCN | N Param.: 17.20 sN Param.: 0.72 |
|
Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 |
4-(dimethylamino)pyridine (in MeCN)  |
MeCN | N Param.: 15.51 sN Param.: 0.62 |
|
J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
5-amino-indole  |
MeCN | N Param.: 7.22 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole  |
MeCN | N Param.: 6.44 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-indole  |
MeCN | N Param.: 6.00 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-indole  |
MeCN | N Param.: 4.42 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-bromo-indole  |
MeCN | N Param.: 4.38 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-cyano-indole  |
MeCN | N Param.: 2.83 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1H-indole-5-carboxylic acid  |
MeCN | N Param.: 3.97 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-2-methylindole  |
MeCN | N Param.: 7.26 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2,5-dimethylindole  |
MeCN | N Param.: 7.22 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-methylindole  |
MeCN | N Param.: 6.91 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-2-methylindole  |
MeCN | N Param.: 6.08 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
4-methoxy-indole  |
MeCN | N Param.: 5.41 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
7-azaindole  |
MeCN | N Param.: 3.87 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
4-chloroaniline (in MeCN)  |
MeCN | N Param.: 12.92 sN Param.: 0.60 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in MeCN)  |
MeCN | N Param.: 12.64 sN Param.: 0.68 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluidine (in MeCN)  |
MeCN | N Param.: 13.19 sN Param.: 0.69 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-methoxyaniline (in MeCN)  |
MeCN | N Param.: 13.42 sN Param.: 0.73 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
DABCO (in MeCN)  |
MeCN | N Param.: 18.80 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
quinuclidine (in MeCN)  |
MeCN | N Param.: 20.54 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
2,5-dimethylpyrrole  |
MeCN | N Param.: 8.01 sN Param.: 0.96 |
|
Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
1,2,5-trimethylpyrrole  |
MeCN | N Param.: 8.69 sN Param.: 1.07 |
|
Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
2,4-dimethylpyrrole  |
MeCN | N Param.: 10.67 sN Param.: 0.91 |
|
Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
3-ethyl-2,4-dimethylpyrrole  |
MeCN | N Param.: 11.63 sN Param.: 0.95 |
|
Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
DBU (in MeCN)  |
MeCN | N Param.: 15.29 sN Param.: 0.70 |
|
Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
DBN (in MeCN)  |
MeCN | N Param.: 16.28 sN Param.: 0.67 |
|
Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
cyanate (in MeCN)  |
MeCN | N Param.: 13.60 sN Param.: 0.84 |
|
Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
azulene  |
MeCN | N Param.: 6.66 sN Param.: 1.02 |
|
Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6,6-dimethylfulvene  |
MeCN | N Param.: 3.93 sN Param.: 0.88 |
|
Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(4-dimethylamino-phenyl)fulvene  |
MeCN | N Param.: 6.72 sN Param.: 0.87 |
|
Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |