Carbanions
For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles
Found 155 Molecules.
| Molecule | Solvent | Reactivity Parameters | Classification | Reference (sort by title or year) |
|---|---|---|---|---|
 anion of 2-nitropropane (in water) | water | N Parameter: 10.69 sN Parameter: 0.56 |  | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of nitroethane (in water) | water | N Parameter: 11.25 sN Parameter: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of 5-phenyl Meldrum's acid (in DMSO) | DMSO | N Parameter: 11.54 sN Parameter: 0.95 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of dimedone (in water) | water | N Parameter: 11.77 sN Parameter: 0.63 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Parameter: 12.02 sN Parameter: 1.17 | | Chem. Eur. J. 2014, 20, 11069-11077 DOI: 10.1002/chem.201403161 |
 anion of phenylnitromethane (in H2O) | water | N Parameter: 12.05 sN Parameter: 0.53 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of Meldrum's acid (in water) | water | N Parameter: 12.06 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of nitromethane (in water) | water | N Parameter: 12.06 sN Parameter: 0.53 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of 2-nitropropane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 12.20 sN Parameter: 0.71 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of 5-(p-anisyl) Meldrum's acid (in DMSO) | DMSO | N Parameter: 12.35 sN Parameter: 0.90 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of phenylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 12.51 sN Parameter: 0.67 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of p-tolylnitromethane (in water) | water | N Parameter: 13.09 sN Parameter: 0.50 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of (4-cyanophenyl)nitromethane (in water) | water | N Parameter: 13.23 sN Parameter: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of nitroethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.41 sN Parameter: 0.67 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of (4-nitrophenyl)nitromethane (in water) | water | N Parameter: 13.58 sN Parameter: 0.52 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of p-tolylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.58 sN Parameter: 0.64 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of diethyl 2-(benzoyl)malonate (in DMSO) | DMSO | N Parameter: 13.63 sN Parameter: 0.80 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of acetylacetone (in water) | water | N Parameter: 13.73 sN Parameter: 0.64 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Parameter: 13.79 sN Parameter: 0.86 | | Chem. Eur. J. 2014, 20, 11069-11077 DOI: 10.1002/chem.201403161 |
 anion of diethyl 2-(acetyl)malonate (in DMSO) | DMSO | N Parameter: 13.83 sN Parameter: 0.84 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of Meldrums acid (in DMSO) | DMSO | N Parameter: 13.91 sN Parameter: 0.86 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 anion of 2-nitro-1-phenylethan-1-one (in DMSO) | DMSO | N Parameter: 13.91 sN Parameter: 0.76 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of (4-cyanophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.92 sN Parameter: 0.74 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of nitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 14.02 sN Parameter: 0.61 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of (4-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 14.05 sN Parameter: 0.72 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 2-thiobarbiturate anion (in DMSO) | DMSO | N Parameter: 14.24 sN Parameter: 0.82 | | J. Org. Chem. 2017, 82, 8476-8488 DOI: 10.1021/acs.joc.7b01223 |
 anion of (3-nitrophenyl)nitromethane (in water) | water | N Parameter: 14.25 sN Parameter: 0.46 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of 3-methyl acetylacetone (in water) | water | N Parameter: 14.33 sN Parameter: 0.69 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO) | DMSO | N Parameter: 14.46 sN Parameter: 0.91 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Parameter: 14.48 sN Parameter: 0.86 | | Chem. Eur. J. 2014, 20, 11069-11077 DOI: 10.1002/chem.201403161 |
 anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Parameter: 14.49 sN Parameter: 0.86 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of (3-nitrophenyl)nitromethane (in 91M9AN) | MeOH-MeCN mix | N Parameter: 14.75 sN Parameter: 0.71 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 1,3-diethyl-thiobarbiturate anion (in DMSO) | DMSO | N Parameter: 14.90 sN Parameter: 0.80 | | J. Org. Chem. 2017, 82, 8476-8488 DOI: 10.1021/acs.joc.7b01223 |
 anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO) | DMSO | N Parameter: 14.94 sN Parameter: 0.96 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO) | DMSO | N Parameter: 14.99 sN Parameter: 0.83 | | Eur. J. Org. Chem. 2017, , 1196-1202 DOI: 10.1002/ejoc.201601513 |
 5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Parameter: 15.02 sN Parameter: 0.75 | | Chem. Eur. J. 2014, 20, 11069-11077 DOI: 10.1002/chem.201403161 |
 anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO) | DMSO | N Parameter: 15.07 sN Parameter: 0.79 | | Eur. J. Org. Chem. 2017, , 1196-1202 DOI: 10.1002/ejoc.201601513 |
 5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Parameter: 15.13 sN Parameter: 0.75 | | Chem. Eur. J. 2014, 20, 11069-11077 DOI: 10.1002/chem.201403161 |
 anion of ethyl 2-nitroacetate (in DMSO) | DMSO | N Parameter: 15.24 sN Parameter: 0.74 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of triethyl methanetricarboxylate (in DMSO) | DMSO | N Parameter: 15.33 sN Parameter: 0.72 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of ethyl cyanoacetate (in water) | water | N Parameter: 15.57 sN Parameter: 0.58 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of 2-phenylmalononitrile (in DMSO) | DMSO | N Parameter: 15.58 sN Parameter: 1.00 | | Eur. J. Org. Chem. 2017, , 1196-1202 DOI: 10.1002/ejoc.201601513 |
 barbiturate anion (in DMSO) | DMSO | N Parameter: 15.59 sN Parameter: 0.80 | | J. Org. Chem. 2017, 82, 8476-8488 DOI: 10.1021/acs.joc.7b01223 |
 anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN) | MeCN | N Parameter: 15.62 sN Parameter: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 DOI: 10.1021/jacs.0c01960 |
 bis(phenylsulfonyl)methanide (in DMSO) | DMSO | N Parameter: 15.68 sN Parameter: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of ethyl 2-cyano-2-phenylacetate (in DMSO) | DMSO | N Parameter: 15.85 sN Parameter: 1.04 | | Eur. J. Org. Chem. 2017, , 1196-1202 DOI: 10.1002/ejoc.201601513 |
 anion of diethyl 2-phenylmalonate (in DMSO) | DMSO | N Parameter: 15.93 sN Parameter: 0.99 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO) | DMSO | N Parameter: 15.97 sN Parameter: 0.72 | | Eur. J. Org. Chem. 2017, , 1196-1202 DOI: 10.1002/ejoc.201601513 |
 anion of ethyl acetylacetate (in water) | water | N Parameter: 15.99 sN Parameter: 0.62 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of 1-phenylbutane-1,3-dione (in DMSO) | DMSO | N Parameter: 16.03 sN Parameter: 0.86 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) | DMSO | N Parameter: 16.06 sN Parameter: 0.69 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of diethyl malonate (in water) | water | N Parameter: 16.15 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN) | MeCN | N Parameter: 16.15 sN Parameter: 0.99 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 DOI: 10.1021/jacs.0c01960 |
 1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Parameter: 16.26 sN Parameter: 0.83 | | J. Am. Chem. Soc. 2018, 140, 11474-11486 DOI: 10.1021/jacs.8b07147 |
 anion of dimedone (in DMSO) | DMSO | N Parameter: 16.27 sN Parameter: 0.77 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 cyanide (in MeCN) | MeCN | N Parameter: 16.27 sN Parameter: 0.70 | | Angew. Chem. Int. Ed. 2005, 44, 142-145 DOI: 10.1002/anie.200461640 |
 anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Parameter: 16.28 sN Parameter: 0.75 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of (4-nitrophenyl)nitromethane (in DMSO) | DMSO | N Parameter: 16.29 sN Parameter: 0.75 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of 3-oxo-3-phenylpropanenitrile (in DMSO) | DMSO | N Parameter: 16.55 sN Parameter: 0.78 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of diethyl 2-(p-anisyl)malonate (in DMSO) | DMSO | N Parameter: 16.73 sN Parameter: 0.91 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of (4-cyanophenyl)nitromethane (in DMSO) | DMSO | N Parameter: 16.96 sN Parameter: 0.73 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO) | DMSO | N Parameter: 17.00 sN Parameter: 0.74 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO) | DMSO | N Parameter: 17.19 sN Parameter: 0.56 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 methoxybis(phenylsulfonyl)methanide (in DMSO) | DMSO | N Parameter: 17.29 sN Parameter: 0.70 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Parameter: 17.33 sN Parameter: 0.74 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) | DMSO | N Parameter: 17.36 sN Parameter: 0.71 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of 1,3-diphenylpropane-1,3-dione (in DMSO) | DMSO | N Parameter: 17.46 sN Parameter: 0.65 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 fluorobis(phenylsulfonyl)methanide (in DMSO) | DMSO | N Parameter: 17.46 sN Parameter: 0.73 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 1,3-dimethylbarbiturate anion (in DMSO) | DMSO | N Parameter: 17.46 sN Parameter: 0.72 | | J. Org. Chem. 2017, 82, 8476-8488 DOI: 10.1021/acs.joc.7b01223 |
 anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO) | DMSO | N Parameter: 17.52 sN Parameter: 0.74 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of acetylacetone (in DMSO) | DMSO | N Parameter: 17.64 sN Parameter: 0.73 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 anion of diethyl methylmalonate (in water) | water | N Parameter: 17.68 sN Parameter: 0.50 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 MeSO2-CH-CO2Et (in DMSO) | DMSO | N Parameter: 18.00 sN Parameter: 0.66 | | Chem. Eur. J. 2010, 16, 8610-8614 DOI: 10.1002/chem.201001455 |
 anion of (3-nitrophenyl)nitromethane (in DMSO) | DMSO | N Parameter: 18.06 sN Parameter: 0.71 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Parameter: 18.19 sN Parameter: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of malononitrile (in 91M9AN) | MeOH-MeCN mix | N Parameter: 18.21 sN Parameter: 0.69 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of dimethyl malonate (in 91M9AN) | MeOH-MeCN mix | N Parameter: 18.24 sN Parameter: 0.64 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Parameter: 18.24 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of phenylnitromethane (in DMSO) | DMSO | N Parameter: 18.29 sN Parameter: 0.71 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of p-tolylnitromethane (in DMSO) | DMSO | N Parameter: 18.31 sN Parameter: 0.76 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO) | DMSO | N Parameter: 18.32 sN Parameter: 0.84 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 anion of 3-methyl acetylacetone (in DMSO) | DMSO | N Parameter: 18.38 sN Parameter: 0.72 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Parameter: 18.50 sN Parameter: 0.75 | | Org. Biomol. Chem. 2008, 6, 3052-3058 DOI: 10.1039/b805604h |
 (EtO)2P(O)CH(-)CN (in DMSO) | DMSO | N Parameter: 18.57 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2009, 131, 704-714 DOI: 10.1021/ja8056216 |
 anion of ethyl cyanoacetate (in 91M9AN) | MeOH-MeCN mix | N Parameter: 18.59 sN Parameter: 0.65 | | Eur. J. Org. Chem. 2006, , 2530-2537 DOI: 10.1002/ejoc.200500769 |
 1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO) | DMSO | N Parameter: 18.63 sN Parameter: 0.82 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 anion of benzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Parameter: 18.67 sN Parameter: 0.68 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 Ph2P(O)CH(-)CN (in DMSO) | DMSO | N Parameter: 18.69 sN Parameter: 0.72 | | J. Am. Chem. Soc. 2009, 131, 704-714 DOI: 10.1021/ja8056216 |
 anion of diethyl 2-(isopropyl)malonate (in DMSO) | DMSO | N Parameter: 18.74 sN Parameter: 0.71 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Parameter: 18.81 sN Parameter: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of ethyl acetylacetate (in DMSO) | DMSO | N Parameter: 18.82 sN Parameter: 0.69 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) | DMSO | N Parameter: 19.03 sN Parameter: 0.58 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Parameter: 19.15 sN Parameter: 0.59 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 Ph2P(O)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 19.20 sN Parameter: 0.69 | | J. Am. Chem. Soc. 2009, 131, 704-714 DOI: 10.1021/ja8056216 |
 (EtO)2P(O)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 19.23 sN Parameter: 0.65 | | J. Am. Chem. Soc. 2009, 131, 704-714 DOI: 10.1021/ja8056216 |
 anion of diethyl 2-cyclohexylmalonate (in DMSO) | DMSO | N Parameter: 19.23 sN Parameter: 0.67 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO) | DMSO | N Parameter: 19.28 sN Parameter: 0.65 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO) | DMSO | N Parameter: 19.35 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of malononitrile (in DMSO) | DMSO | N Parameter: 19.36 sN Parameter: 0.67 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Parameter: 19.49 sN Parameter: 0.63 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of malononitrile (in water) | water | N Parameter: 19.50 sN Parameter: 0.55 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide | DMSO | N Parameter: 19.53 sN Parameter: 0.83 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO) | DMSO | N Parameter: 19.58 sN Parameter: 0.73 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 enolate of 2-coumaranone (in DMSO) | DMSO | N Parameter: 19.60 sN Parameter: 0.75 | | J. Org. Chem. 2024, 89, 6915-6928 DOI: 10.1021/acs.joc.4c00277 |
 anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) | DMSO | N Parameter: 19.61 sN Parameter: 0.60 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 anion of ethyl cyanoacetate (in DMSO) | DMSO | N Parameter: 19.62 sN Parameter: 0.67 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 anion of 4-nitrobenzyl-CN (in DMSO) | DMSO | N Parameter: 19.67 sN Parameter: 0.68 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN) | MeCN | N Parameter: 19.90 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 DOI: 10.1021/jacs.0c01960 |
 bis(4-nitrophenyl)methanide (in DMSO) | DMSO | N Parameter: 19.92 sN Parameter: 0.67 | | ARKIVOC 2008, (x), 37-53 DOI: 10.3998/ark.5550190.0009.a05 |
 2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 20.00 sN Parameter: 0.71 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO) | DMSO | N Parameter: 20.02 sN Parameter: 0.76 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 1,2,3-trimethoxy-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Parameter: 20.08 sN Parameter: 0.74 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of 4-nitrobenzyl-CN (in MeCN) | MeCN | N Parameter: 20.10 sN Parameter: 0.71 | | J. Am. Chem. Soc. 2020, 142, 8383-8402 DOI: 10.1021/jacs.0c01960 |
 anion of diethyl malonate (in DMSO) | DMSO | N Parameter: 20.22 sN Parameter: 0.65 | | Angew. Chem. Int. Ed. 2002, 41, 91-95 DOI: 10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P |
 2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO) | DMSO | N Parameter: 20.51 sN Parameter: 0.64 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO) | DMSO | N Parameter: 20.60 sN Parameter: 0.63 | | Eur. J. Org. Chem. 2015, , 7594-7601 DOI: 10.1002/ejoc.201501107 |
 anion of 2-nitropropane (in DMSO) | DMSO | N Parameter: 20.61 sN Parameter: 0.69 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 MeSO-CH-CO2Et (in DMSO) | DMSO | N Parameter: 20.61 sN Parameter: 0.64 | | Chem. Eur. J. 2010, 16, 8610-8614 DOI: 10.1002/chem.201001455 |
 1,3-diethoxy-2-fluoro-1,3-dioxopropan-2-ide (in DMSO) | DMSO | N Parameter: 20.63 sN Parameter: 0.76 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 DOI: 10.1002/anie.201605616 |
 anion of nitromethane (in DMSO) | DMSO | N Parameter: 20.71 sN Parameter: 0.60 | | J. Org. Chem. 2004, 69, 7565-7576 DOI: 10.1021/jo048773j |
 anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN) | MeOH-MeCN mix | N Parameter: 20.72 sN Parameter: 0.58 | | J. Am. Chem. Soc. 2007, 129, 9753-9761 DOI: 10.1021/ja072135b |
 anion of diethyl methylmalonate (in DMSO) | DMSO | N Parameter: 21.13 sN Parameter: 0.68 | | J. Am. Chem. Soc. 2003, 125, 12980-12986 DOI: 10.1021/ja036838e |
 anion of nitroethane (in DMSO) | DMSO | N Parameter: 21.54 sN Parameter: 0.62 | | J. Org. Chem. 2003, 68, 6880-6886 DOI: 10.1021/jo0344182 |
 anion of nitroethane (in DMF) | DMF | N Parameter: 22.21 sN Parameter: 0.48 | | Chem. Eur. J. 2008, 14, 6108-6118 DOI: 10.1002/chem.200800329 |
 anion of (4-CN-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Parameter: 22.60 sN Parameter: 0.57 | | Org. Biomol. Chem. 2008, 6, 3052-3058 DOI: 10.1039/b805604h |
 anion of diethyl 2-butylmalonate (in DMSO) | DMSO | N Parameter: 23.00 sN Parameter: 0.55 | | Eur. J. Org. Chem. 2016, , 1841-1848 DOI: 10.1002/ejoc.201600107 |
 anion of 1,2-diphenylethanone (in DMSO) | DMSO | N Parameter: 23.15 sN Parameter: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 2-(pyrid-4-yl)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 23.27 sN Parameter: 0.70 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 2-(4-CN-C6H4)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 23.64 sN Parameter: 0.65 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 lithium indenide (in DMSO) | DMSO | N Parameter: 23.66 sN Parameter: 0.70 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 DOI: 10.1002/anie.201501385 |
 sodium indenide (in DMSO) | DMSO | N Parameter: 23.74 sN Parameter: 0.71 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 DOI: 10.1002/anie.201501385 |
 bromo(phenylsulfonyl)methanide (in DMSO) | DMSO | N Parameter: 23.90 sN Parameter: 0.62 | | J. Org. Chem. 2017, 82, 2011-2017 DOI: 10.1021/acs.joc.6b02844 |
 potassium indenide (in DMSO) | DMSO | N Parameter: 24.16 sN Parameter: 0.68 | | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 DOI: 10.1002/anie.201501385 |
 anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Parameter: 24.30 sN Parameter: 0.51 | | Org. Biomol. Chem. 2008, 6, 3052-3058 DOI: 10.1039/b805604h |
 chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Parameter: 24.88 sN Parameter: 0.49 | | J. Org. Chem. 2017, 82, 2011-2017 DOI: 10.1021/acs.joc.6b02844 |
 anion of 1-phenylpropan-2-one (in DMSO) | DMSO | N Parameter: 24.99 sN Parameter: 0.60 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 anion of 4-cyanobenzyl-CN (in DMSO) | DMSO | N Parameter: 25.11 sN Parameter: 0.54 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 anion of 2-(4-CN-C6H4)propionitrile (in DMSO) | DMSO | N Parameter: 25.35 sN Parameter: 0.56 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 enolate of 3-isochromanone (in DMSO) | DMSO | N Parameter: 25.39 sN Parameter: 0.54 | | J. Org. Chem. 2024, 89, 6915-6928 DOI: 10.1021/acs.joc.4c00277 |
 chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Parameter: 25.59 sN Parameter: 0.51 | | J. Org. Chem. 2017, 82, 2011-2017 DOI: 10.1021/acs.joc.6b02844 |
 anion of (benzylsulfonyl)benzene (in DMSO) | DMSO | N Parameter: 25.77 sN Parameter: 0.56 | | Chem. Eur. J. 2015, 21, 875-884 DOI: 10.1002/chem.201404500 |
 chloro(phenylsulfonyl)methanide (in DMF) | DMF | N Parameter: 26.64 sN Parameter: 0.64 |  | Chem. Eur. J. 2008, 14, 6108-6118 DOI: 10.1002/chem.200800329 |
 chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Parameter: 26.90 sN Parameter: 0.45 | | J. Org. Chem. 2017, 82, 2011-2017 DOI: 10.1021/acs.joc.6b02844 |
 1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Parameter: 26.95 sN Parameter: 0.52 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |
 anion of 4-(trifluoromethyl)benzyl-CN (in DMSO) | DMSO | N Parameter: 27.28 sN Parameter: 0.50 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 2-PhCH(-)CO2Et (in DMSO) | DMSO | N Parameter: 27.54 sN Parameter: 0.57 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 27.57 sN Parameter: 0.53 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 2-(4-Br-C6H4)CH(-)CO2Et (in DMSO) | DMSO | N Parameter: 27.62 sN Parameter: 0.53 | | Eur. J. Org. Chem. 2013, , 4255-4261 DOI: 10.1002/ejoc.201300265 |
 2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO) | DMSO | N Parameter: 27.77 sN Parameter: 0.47 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |
 chloro(phenylsulfonyl)methanide (in DMSO) | DMSO | N Parameter: 28.27 sN Parameter: 0.42 | | J. Org. Chem. 2017, 82, 2011-2017 DOI: 10.1021/acs.joc.6b02844 |
 anion of 2-phenyl-propionitrile (in DMSO) | DMSO | N Parameter: 28.95 sN Parameter: 0.58 | | J. Org. Chem. 2009, 74, 75-81 DOI: 10.1021/jo802241x |
 1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Parameter: 29.02 sN Parameter: 0.49 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |
 1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Parameter: 29.10 sN Parameter: 0.50 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |
 cyano((diphenylmethylene)amino)methanide | DMSO | N Parameter: 29.50 sN Parameter: 0.50 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |
 2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO) | DMSO | N Parameter: 30.82 sN Parameter: 0.41 | | Tetrahedron 2019, 75, 459-463 DOI: 10.1016/j.tet.2018.11.075 |