Carbanions

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Name	Solvent	Reactivity Parameters	Reference (title or year)
anion of malononitrile (in water)	water	N Param.: 19.50 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.60	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
anion of ethyl cyanoacetate (in DMSO)	DMSO	N Param.: 19.62 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.69	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
MeSO-CH-CO2Et (in DMSO)	DMSO	N Param.: 20.61 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.68	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of nitroethane (in DMSO)	DMSO	N Param.: 21.54 s_N Param.: 0.62	J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182
anion of nitroethane (in DMF)	DMF	N Param.: 22.21 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.65	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
lithium indenide (in DMSO)	DMSO	N Param.: 23.66 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
sodium indenide (in DMSO)	DMSO	N Param.: 23.74 s_N 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 s_N Param.: 0.62	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
potassium indenide (in DMSO)	DMSO	N Param.: 24.16 s_N 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 s_N 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 s_N 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 s_N 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 s_N 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 s_N Param.: 0.56	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
enolate of 3-isochromanone (in DMSO)	DMSO	N Param.: 25.39 s_N 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 s_N 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 s_N Param.: 0.56	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N 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 s_N 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 s_N 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 s_N Param.: 0.50	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
2-PhCH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.54 s_N 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 s_N 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 s_N 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 s_N Param.: 0.47	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
chloro(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 28.27 s_N Param.: 0.42	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844