C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
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 |
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 |
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 |
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 |
cyanide (in MeCN) |
MeCN | N Param.: 16.27 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 |
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 |
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 |
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 |
6-(julolidin-9-yl)fulvene |
MeCN | N Param.: 7.79 sN Param.: 1.06 | | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
(cyclohexen-1-yl)prolinate (in MeCN) |
MeCN | N Param.: 18.86 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
1-(N-pyrrolidino)cyclohexene (in MeCN) |
MeCN | N Param.: 16.42 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
methyl (cyclohexen-1-yl)prolinate (in MeCN) |
MeCN | N Param.: 14.96 sN Param.: 0.68 | | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
1-(N-piperidino)cyclohexene (in MeCN) |
MeCN | N Param.: 14.02 sN Param.: 0.76 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) |
MeCN | N Param.: 12.34 sN Param.: 0.72 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN) |
MeCN | N Param.: 10.52 sN Param.: 0.78 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.88 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(5-methyl-furan-2-yl) pinacol boronate |
MeCN | N Param.: 2.90 sN Param.: 0.98 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) MDA boronate |
MeCN | N Param.: 6.38 sN Param.: 0.86 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) MIDA boronate |
MeCN | N Param.: 1.84 sN Param.: 1.26 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl) trifluoroborate |
MeCN | N Param.: 7.66 sN Param.: 1.04 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
tetrakis(5-methyl-furan-2-yl)borate |
MeCN | N Param.: 9.09 sN Param.: 1.12 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate |
MeCN | N Param.: 12.55 sN Param.: 0.92 | | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a |
N-(1-phenylvinyl)acetamide |
MeCN | N Param.: 5.73 sN Param.: 0.97 | | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |