Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
(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 | |
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 | |
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 | |
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 | |
azide ion (in 91nPr9AN) | nPrOH-MeCN mix | N Param.: 16.70 sN Param.: 0.73 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
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 | |
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 | |
chloride (in 50/50 MeOH/MeCN) | MeOH-MeCN mix | N Param.: 14.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
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 | |
anion of nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.02 sN Param.: 0.61 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of nitroethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of 2-nitropropane (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.20 sN Param.: 0.71 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of phenylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.51 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of p-tolylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.58 sN Param.: 0.64 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of (4-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.05 sN Param.: 0.72 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of (3-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.75 sN Param.: 0.71 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of (4-cyanophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.92 sN Param.: 0.74 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of ethyl cyanoacetate (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.59 sN Param.: 0.65 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of malononitrile (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.21 sN Param.: 0.69 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
anion of dimethyl malonate (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.64 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
azide ion (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
azide ion (in 45M55AN) | MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
pyrrolidine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
piperidine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
morpholine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
diethanolamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.71 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
hydrazine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.47 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
trimethyl phosphite (in 91M9AN) | MeOH-MeCN mix | N Param.: 9.04 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
2,2,2-trifluoroethylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 10.20 sN Param.: 0.92 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
imidazole (in 91M9AN) | MeOH-MeCN mix | N Param.: 10.41 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
hydroxylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.23 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
ethanolamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.23 sN Param.: 0.65 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
benzylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.46 sN Param.: 0.62 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
n-propylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
4-(dimethylamino)pyridine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.20 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.66 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 19.49 sN Param.: 0.63 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Param.: 20.72 sN Param.: 0.58 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
methanol | MeOH | N Param.: 7.54 sN Param.: 0.92 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
chloride (in MeOH) | MeOH | N Param.: 12.90 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
methanolate (in methanol) | MeOH | N Param.: 15.78 sN Param.: 0.56 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
fluoride (in MeOH) | MeOH | N Param.: 11.31 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
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 |