Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
trifluoroethanol![]() ![]() |
TFE | N Param.: 1.11 sN Param.: 0.96 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
chloride (in CF3CH2OH)![]() ![]() |
TFE | N Param.: 10.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in CF3CH2OH)![]() ![]() |
TFE | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF) ![]() ![]() |
THF | N Param.: 21.72 sN Param.: 0.45 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 23.35 sN Param.: 0.40 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 14.07 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
triphenylphosphine (in THF)![]() ![]() |
THF | N Param.: 13.59 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
4-(dimethylamino)pyridine (in THF)![]() ![]() |
THF | N Param.: 15.90 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
DBU (in THF)![]() ![]() |
THF | N Param.: 16.12 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
MeO-Breslow 1a![]() ![]() |
THF | N Param.: 14.77 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1b![]() ![]() |
THF | N Param.: 10.45 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1c![]() ![]() |
THF | N Param.: 16.61 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1e![]() ![]() |
THF | N Param.: 15.65 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Dexoxy Breslow intermediate 6![]() ![]() |
THF | N Param.: 15.58 sN Param.: 0.57 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Desoxy Breslow intermediate 2a![]() ![]() |
THF | N Param.: 17.12 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2a'![]() ![]() |
THF | N Param.: 14.45 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b![]() ![]() |
THF | N Param.: 13.91 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b'![]() ![]() |
THF | N Param.: 11.42 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2c'![]() ![]() |
THF | N Param.: 12.75 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)![]() ![]() |
THF | N Param.: 15.33 sN Param.: 0.79 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)![]() ![]() |
THF | N Param.: 15.92 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
(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.: 14.40 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
(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 | |
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 21.50 sN Param.: 0.45 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 16.54 sN Param.: 0.47 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 20.41 sN Param.: 0.46 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 23.00 sN Param.: 0.46 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
1,3-dimethyl-2-methyleneimidazolidine (in THF)![]() ![]() |
THF | N Param.: 18.11 sN Param.: 0.68 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)![]() ![]() |
THF | N Param.: 18.68 sN Param.: 0.63 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)![]() ![]() |
THF | N Param.: 17.80 sN Param.: 0.79 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole![]() ![]() |
THF | N Param.: 19.84 sN Param.: 0.58 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)![]() ![]() |
THF | N Param.: 21.36 sN Param.: 0.42 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-Bis(2,6-diisopropylphenyl)-4-methylene-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 22.30 sN Param.: 0.49 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-Bis(2,6-diisopropylphenyl)-5-(4-methoxyphenyl)-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 23.55 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)![]() ![]() |
THF | N Param.: 20.78 sN Param.: 0.61 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-Diisopropyl-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 30.25 sN Param.: 0.54 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 31.92 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-bis(2,6-diisopropylphenyl)-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 22.80 sN Param.: 0.60 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1,3-bis(2,6-diisopropylphenyl)-5-methyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 24.86 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 | |
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 26.16 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283 | |
Se-HyperBTM (in THF)![]() ![]() |
THF | N Param.: 14.19 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
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 water)![]() ![]() |
water | N Param.: 10.47 sN Param.: 0.61 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
semicarbazide (in water)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.52 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
hydroxylamine (in water)![]() ![]() |
water | N Param.: 11.41 sN Param.: 0.55 | 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 | |
n-propylamine (in water)![]() ![]() |
water | N Param.: 13.33 sN Param.: 0.56 | 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 | |
SO3(2-) (in water)![]() ![]() |
water | N Param.: 16.83 sN Param.: 0.56 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
2-sulfidoacetate (in water)![]() ![]() |
water | N Param.: 22.62 sN Param.: 0.43 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
anion of Meldrum's acid (in water)![]() ![]() |
water | N Param.: 12.06 sN Param.: 0.66 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of dimedone (in water)![]() ![]() |
water | N Param.: 11.77 sN Param.: 0.63 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of acetylacetone (in water)![]() ![]() |
water | N Param.: 13.73 sN Param.: 0.64 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of ethyl acetylacetate (in water)![]() ![]() |
water | N Param.: 15.99 sN Param.: 0.62 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of malononitrile (in water)![]() ![]() |
water | N Param.: 19.50 sN Param.: 0.55 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of ethyl cyanoacetate (in water)![]() ![]() |
water | N Param.: 15.57 sN Param.: 0.58 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of diethyl malonate (in water)![]() ![]() |
water | N Param.: 16.15 sN Param.: 0.66 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of diethyl methylmalonate (in water)![]() ![]() |
water | N Param.: 17.68 sN Param.: 0.50 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of 3-methyl acetylacetone (in water)![]() ![]() |
water | N Param.: 14.33 sN Param.: 0.69 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
anion of nitroethane (in water)![]() ![]() |
water | N Param.: 11.25 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of nitromethane (in water)![]() ![]() |
water | N Param.: 12.06 sN Param.: 0.53 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of 2-nitropropane (in water)![]() ![]() |
water | N Param.: 10.69 sN Param.: 0.56 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of phenylnitromethane (in H2O)![]() ![]() |
water | N Param.: 12.05 sN Param.: 0.53 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of p-tolylnitromethane (in water)![]() ![]() |
water | N Param.: 13.09 sN Param.: 0.50 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.58 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (3-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 14.25 sN Param.: 0.46 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-cyanophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.23 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
chloride (in H2O)![]() ![]() |
water | N Param.: 10.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in H2O)![]() ![]() |
water | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
4-chloropyridine (in H2O)![]() ![]() |
water | N Param.: 10.50 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
pyridine (in H2O)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methylpyridine (in H2O)![]() ![]() |
water | N Param.: 11.10 sN Param.: 0.75 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxypyridine (in H2O)![]() ![]() |
water | N Param.: 11.44 sN Param.: 0.68 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-aminopyridine (in H2O)![]() ![]() |
water | N Param.: 12.19 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in H2O)![]() ![]() |
water | N Param.: 13.19 sN Param.: 0.56 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-pyrrolidinopyridine (in H2O)![]() ![]() |
water | N Param.: 12.39 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
ammonia (in water)![]() ![]() |
water | N Param.: 9.48 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methylamine (in water)![]() ![]() |
water | N Param.: 13.85 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethylamine (in water)![]() ![]() |
water | N Param.: 12.87 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
isopropylamine (in water)![]() ![]() |
water | N Param.: 12.00 sN Param.: 0.56 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
tert-butylamine (in water)![]() ![]() |
water | N Param.: 10.48 sN Param.: 0.65 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
dimethylamine (in water)![]() ![]() |
water | N Param.: 17.12 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
diethylamine (in water)![]() ![]() |
water | N Param.: 14.68 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
pyrrolidine (in water)![]() ![]() |
water | N Param.: 17.21 sN Param.: 0.49 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperidine (in water)![]() ![]() |
water | N Param.: 18.13 sN Param.: 0.44 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
morpholine (in water)![]() ![]() |
water | N Param.: 15.62 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperazine (in water)![]() ![]() |
water | N Param.: 17.22 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
perhydroazepine (in water)![]() ![]() |
water | N Param.: 18.29 sN Param.: 0.46 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycinenitrile (in water)![]() ![]() |
water | N Param.: 10.80 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethanolamine (in water)![]() ![]() |
water | N Param.: 12.61 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethylenediamine (in water)![]() ![]() |
water | N Param.: 13.28 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
propargylamine (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
allylamine (in water)![]() ![]() |
water | N Param.: 13.21 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
benzylamine (in water)![]() ![]() |
water | N Param.: 13.44 sN Param.: 0.55 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
aniline (in water)![]() ![]() |
water | N Param.: 12.99 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
p-toluidine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.79 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
4-methoxyaniline (in water)![]() ![]() |
water | N Param.: 14.28 sN Param.: 0.68 | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 | |
diethanolamine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
N-methyl-glycinenitrile (in water)![]() ![]() |
water | N Param.: 13.50 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methyl glycinate (in water)![]() ![]() |
water | N Param.: 12.08 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |





































































































