C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
Me2S=CH(4-CN-C6H4) (in DMSO) | DMSO | N Param.: 21.07 sN Param.: 0.68 | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | |
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 | |
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 | |
anion of nitromethane (in DMSO) | DMSO | N Param.: 20.71 sN Param.: 0.60 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
1,3-diethoxy-2-fluoro-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Param.: 20.63 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
anion of 2-nitropropane (in DMSO) | DMSO | N Param.: 20.61 sN Param.: 0.69 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
MeSO-CH-CO2Et (in DMSO) | DMSO | N Param.: 20.61 sN Param.: 0.64 | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | |
1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO) | DMSO | N Param.: 20.60 sN Param.: 0.63 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Param.: 20.51 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
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.[...] | |
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO) | DMSO | N Param.: 20.24 sN Param.: 0.60 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
anion of diethyl malonate (in DMSO) | DMSO | N Param.: 20.22 sN Param.: 0.65 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
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 | |
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 | |
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 | |
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 | |
bis(4-nitrophenyl)methanide (in DMSO) | DMSO | N Param.: 19.92 sN Param.: 0.67 | ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] | |
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 | |
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-nitrobenzyl-CN (in DMSO) | DMSO | N Param.: 19.67 sN Param.: 0.68 | 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 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 | |
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 | |
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 | |
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 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 | |
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 | |
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 | |
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[...] | |
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 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 | |
(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 | |
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 | |
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 | |
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 | |
(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 | |
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[...] | |
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 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 | |
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 | |
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 | |
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-(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 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 | |
(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 (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 | |
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 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 |