C-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
anion of ethyl 2-nitroacetate (in DMSO)  |
DMSO | N Param.: 15.24 sN Param.: 0.74 |  | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
3-pyrrolidino-1H-indene (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.93 | | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
(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 |
anion of triethyl methanetricarboxylate (in DMSO) |
DMSO | N Param.: 15.33 sN Param.: 0.72 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
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 |
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 |
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 |
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 |
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO) |
DMSO | N Param.: 15.60 sN Param.: 0.51 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN) |
MeCN | N Param.: 15.62 sN Param.: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
MeO-Breslow 1e |
THF | N Param.: 15.65 sN Param.: 0.52 | | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO) |
DMSO | N Param.: 15.68 sN Param.: 0.65 | | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 |
bis(phenylsulfonyl)methanide (in DMSO) |
DMSO | N Param.: 15.68 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
Me2S=CH-CO2Et (in DMSO) |
DMSO | N Param.: 15.85 sN Param.: 0.61 | | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
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 |
1-(N-pyrrolidino)cyclopentene |
dichloromethane | N Param.: 15.91 sN Param.: 0.86 | | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(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 |
anion of diethyl 2-phenylmalonate (in DMSO) |
DMSO | N Param.: 15.93 sN Param.: 0.99 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
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 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 1-phenylbutane-1,3-dione (in DMSO) |
DMSO | N Param.: 16.03 sN Param.: 0.86 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 16.06 sN Param.: 0.69 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
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 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN) |
MeCN | N Param.: 16.15 sN Param.: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
Me2S=CH-CN (in DMSO) |
DMSO | N Param.: 16.23 sN Param.: 0.60 | | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
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 |
anion of dimedone (in DMSO) |
DMSO | N Param.: 16.27 sN Param.: 0.77 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
cyanide (in MeCN) |
MeCN | N Param.: 16.27 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO) |
DMSO | N Param.: 16.28 sN Param.: 0.75 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of (4-nitrophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 16.29 sN Param.: 0.75 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
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 |
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.[...] |
anion of 3-oxo-3-phenylpropanenitrile (in DMSO) |
DMSO | N Param.: 16.55 sN Param.: 0.78 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
MeO-Breslow 1c |
THF | N Param.: 16.61 sN Param.: 0.68 | | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 |
anion of diethyl 2-(p-anisyl)malonate (in DMSO) |
DMSO | N Param.: 16.73 sN Param.: 0.91 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
anion of (4-cyanophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 16.96 sN Param.: 0.73 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO) |
DMSO | N Param.: 17.00 sN Param.: 0.74 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
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 |
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO) |
DMSO | N Param.: 17.19 sN Param.: 0.56 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
methoxybis(phenylsulfonyl)methanide (in DMSO) |
DMSO | N Param.: 17.29 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO) |
DMSO | N Param.: 17.33 sN Param.: 0.74 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 17.36 sN Param.: 0.71 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
Desoxy Breslow intermediate 2a |
DMSO | N Param.: 17.41 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 |
anion of 1,3-diphenylpropane-1,3-dione (in DMSO) |
DMSO | N Param.: 17.46 sN Param.: 0.65 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
fluorobis(phenylsulfonyl)methanide (in DMSO) |
DMSO | N Param.: 17.46 sN Param.: 0.73 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
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 |
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO) |
DMSO | N Param.: 17.52 sN Param.: 0.74 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of acetylacetone (in DMSO) |
DMSO | N Param.: 17.64 sN Param.: 0.73 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
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 |
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-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) |
DMSO | N Param.: 17.98 sN Param.: 0.63 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
MeSO2-CH-CO2Et (in DMSO) |
DMSO | N Param.: 18.00 sN Param.: 0.66 | | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
anion of (3-nitrophenyl)nitromethane (in DMSO) |
DMSO | N Param.: 18.06 sN Param.: 0.71 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO) |
DMSO | N Param.: 18.10 sN Param.: 0.46 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
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 |
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO) |
DMSO | N Param.: 18.19 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
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 phenylnitromethane (in DMSO) |
DMSO | N Param.: 18.29 sN Param.: 0.71 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of p-tolylnitromethane (in DMSO) |
DMSO | N Param.: 18.31 sN Param.: 0.76 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO) |
DMSO | N Param.: 18.32 sN Param.: 0.84 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
anion of 3-methyl acetylacetone (in DMSO) |
DMSO | N Param.: 18.38 sN Param.: 0.72 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
Me2S=CH(p-NO2-C6H4) (in DMSO) |
DMSO | N Param.: 18.42 sN Param.: 0.65 | | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 |
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO) |
DMSO | N Param.: 18.50 sN Param.: 0.75 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
(EtO)2P(O)CH(-)CN (in DMSO) |
DMSO | N Param.: 18.57 sN Param.: 0.66 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
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 |
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO) |
DMSO | N Param.: 18.63 sN Param.: 0.82 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
anion of benzyl trifluoromethyl sulfone (in DMSO) |
DMSO | N Param.: 18.67 sN Param.: 0.68 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
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 |
Ph2P(O)CH(-)CN (in DMSO) |
DMSO | N Param.: 18.69 sN Param.: 0.72 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
anion of diethyl 2-(isopropyl)malonate (in DMSO) |
DMSO | N Param.: 18.74 sN Param.: 0.71 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 18.81 sN Param.: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
anion of ethyl acetylacetate (in DMSO) |
DMSO | N Param.: 18.82 sN Param.: 0.69 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
(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 |
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 19.03 sN Param.: 0.58 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.15 sN Param.: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
Ph2P(O)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 19.20 sN Param.: 0.69 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
(EtO)2P(O)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 19.23 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
anion of diethyl 2-cyclohexylmalonate (in DMSO) |
DMSO | N Param.: 19.23 sN Param.: 0.67 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO) |
DMSO | N Param.: 19.28 sN Param.: 0.65 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO) |
DMSO | N Param.: 19.35 sN Param.: 0.67 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of malononitrile (in DMSO) |
DMSO | N Param.: 19.36 sN Param.: 0.67 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.38 sN Param.: 0.50 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO) |
DMSO | N Param.: 19.46 sN Param.: 0.58 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
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 malononitrile (in water) |
water | N Param.: 19.50 sN Param.: 0.55 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide |
DMSO | N Param.: 19.53 sN Param.: 0.83 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO) |
DMSO | N Param.: 19.58 sN Param.: 0.73 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) |
DMSO | N Param.: 19.61 sN Param.: 0.60 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of ethyl cyanoacetate (in DMSO) |
DMSO | N Param.: 19.62 sN Param.: 0.67 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
anion of 4-nitrobenzyl-CN (in DMSO) |
DMSO | N Param.: 19.67 sN Param.: 0.68 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
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 |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN) |
MeCN | N Param.: 19.90 sN Param.: 0.66 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
bis(4-nitrophenyl)methanide (in DMSO) |
DMSO | N Param.: 19.92 sN Param.: 0.67 | | ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] |
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 20.00 sN Param.: 0.71 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO) |
DMSO | N Param.: 20.02 sN Param.: 0.76 | | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) |
DMSO | N Param.: 20.08 sN Param.: 0.57 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
1,2,3-trimethoxy-1,3-dioxopropan-2-ide (in DMSO) |
DMSO | N Param.: 20.08 sN Param.: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
anion of 4-nitrobenzyl-CN (in MeCN) |
MeCN | N Param.: 20.10 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |