Carbanions
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
enolate of 2-coumaranone (in DMSO) |
DMSO | N Param.: 19.60 sN Param.: 0.75 | | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
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 |
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 |
1,2,3-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 |
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[...] |
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 |
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 |
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 |
1,3-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 nitromethane (in DMSO) |
DMSO | N Param.: 20.71 sN Param.: 0.60 | | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
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 diethyl methylmalonate (in DMSO) |
DMSO | N Param.: 21.13 sN Param.: 0.68 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of nitroethane (in DMSO) |
DMSO | N Param.: 21.54 sN Param.: 0.62 | | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
anion of nitroethane (in DMF) |
DMF | N Param.: 22.21 sN Param.: 0.48 | | Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329 |
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO) |
DMSO | N Param.: 22.60 sN Param.: 0.57 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
anion of diethyl 2-butylmalonate (in DMSO) |
DMSO | N Param.: 23.00 sN Param.: 0.55 | | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
anion of 1,2-diphenylethanone (in DMSO) |
DMSO | N Param.: 23.15 sN Param.: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 23.27 sN Param.: 0.70 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 23.64 sN Param.: 0.65 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
lithium indenide (in DMSO) |
DMSO | N Param.: 23.66 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
sodium indenide (in DMSO) |
DMSO | N Param.: 23.74 sN Param.: 0.71 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
bromo(phenylsulfonyl)methanide (in DMSO) |
DMSO | N Param.: 23.90 sN Param.: 0.62 | | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
potassium indenide (in DMSO) |
DMSO | N Param.: 24.16 sN Param.: 0.68 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO) |
DMSO | N Param.: 24.30 sN Param.: 0.51 | | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO) |
DMSO | N Param.: 24.88 sN Param.: 0.49 | | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
anion of 1-phenylpropan-2-one (in DMSO) |
DMSO | N Param.: 24.99 sN Param.: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 4-cyanobenzyl-CN (in DMSO) |
DMSO | N Param.: 25.11 sN Param.: 0.54 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO) |
DMSO | N Param.: 25.35 sN Param.: 0.56 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
enolate of 3-isochromanone (in DMSO) |
DMSO | N Param.: 25.39 sN Param.: 0.54 | | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO) |
DMSO | N Param.: 25.59 sN Param.: 0.51 | | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
anion of (benzylsulfonyl)benzene (in DMSO) |
DMSO | N Param.: 25.77 sN Param.: 0.56 | | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
chloro(phenylsulfonyl)methanide (in DMF) |
DMF | N Param.: 26.64 sN Param.: 0.64 |  | Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329 |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO) |
DMSO | N Param.: 26.90 sN Param.: 0.45 | | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 26.95 sN Param.: 0.52 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO) |
DMSO | N Param.: 27.28 sN Param.: 0.50 | | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
2-PhCH(-)CO2Et (in DMSO) |
DMSO | N Param.: 27.54 sN Param.: 0.57 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 27.57 sN Param.: 0.53 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO) |
DMSO | N Param.: 27.62 sN Param.: 0.53 | | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO) |
DMSO | N Param.: 27.77 sN Param.: 0.47 | | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
chloro(phenylsulfonyl)methanide (in DMSO) |
DMSO | N Param.: 28.27 sN Param.: 0.42 | | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |