Mayr's Database of Reactivity Parameters

Carbanions

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles
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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
enolate of 3-isochromanone (in DMSO)
C9H7O2-*
 DMSO

N  Param.: 25.39

sN Param.: 0.54		***J. Org. Chem. 2024, 89, 6915-6928
10.1021/acs.joc.4c00277
enolate of 2-coumaranone (in DMSO)
C8H5O2-*
 DMSO

N  Param.: 19.60

sN Param.: 0.75		***J. Org. Chem. 2024, 89, 6915-6928
10.1021/acs.joc.4c00277
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)
C9H5F6O2S*
 MeCN

N  Param.: 16.15

sN Param.: 0.99		***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)
C9H5F3NO2S*
 MeCN

N  Param.: 15.62

sN Param.: 0.99		***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-nitrobenzyl-CN (in MeCN)
C8H5N2O2*
 MeCN

N  Param.: 20.10

sN Param.: 0.71		***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)
C13H10NO4S*
 MeCN

N  Param.: 19.90

sN Param.: 0.66		***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
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[...]
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)
C19H20NO2-*
 DMSO

N  Param.: 27.77

sN Param.: 0.47		***Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
 DMSO

N  Param.: 29.10

sN Param.: 0.50		*Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
 DMSO

N  Param.: 29.02

sN Param.: 0.49		**Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)
*
 DMSO

N  Param.: 30.82

sN Param.: 0.41		**Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
cyano((diphenylmethylene)amino)methanide
*
 DMSO

N  Param.: 29.50

sN Param.: 0.50		*Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)
C11H10NO5-*
 DMSO

N  Param.: 16.26

sN Param.: 0.83		***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
chloro(phenylsulfonyl)methanide (in DMSO)
C7H6ClO2S*
 DMSO

N  Param.: 28.27

sN Param.: 0.42		***J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
bromo(phenylsulfonyl)methanide (in DMSO)
C7H6BrO2S*
 DMSO

N  Param.: 23.90

sN Param.: 0.62		***J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)
C8H5ClNO2S*
 DMSO

N  Param.: 25.59

sN Param.: 0.51		***J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)
C7H5ClNO4S*
 DMSO

N  Param.: 24.88

sN Param.: 0.49		***J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)
C7H5Cl2O2S*
 DMSO

N  Param.: 26.90

sN Param.: 0.45		***J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)
C11H10NO2*
 DMSO

N  Param.: 15.85

sN Param.: 1.04		***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of 2-phenylmalononitrile (in DMSO)
C9H5N2*
 DMSO

N  Param.: 15.58

sN Param.: 1.00		***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)
C14H10NO2S*
 DMSO

N  Param.: 15.97

sN Param.: 0.72		***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)
C19H15O4S2*
 DMSO

N  Param.: 15.07

sN Param.: 0.79		***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)
C21H15O2*
 DMSO

N  Param.: 14.99

sN Param.: 0.83		***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
barbiturate anion (in DMSO)
C4H3N2O3*
 DMSO

N  Param.: 15.59

sN Param.: 0.80		***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
1,3-dimethylbarbiturate anion (in DMSO)
C6H7N2O3*
 DMSO

N  Param.: 17.46

sN Param.: 0.72		***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
2-thiobarbiturate anion (in DMSO)
C4H3N2O2S*
 DMSO

N  Param.: 14.24

sN Param.: 0.82		***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
1,3-diethyl-thiobarbiturate anion (in DMSO)
C8H11N2O2S*
 DMSO

N  Param.: 14.90

sN Param.: 0.80		***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
anion of diethyl 2-(isopropyl)malonate (in DMSO)
C10H17O4*
 DMSO

N  Param.: 18.74

sN Param.: 0.71		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-butylmalonate (in DMSO)
C11H19O4*
 DMSO

N  Param.: 23.00

sN Param.: 0.55		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-cyclohexylmalonate (in DMSO)
C13H21O4*
 DMSO

N  Param.: 19.23

sN Param.: 0.67		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-phenylmalonate (in DMSO)
C13H15O4*
 DMSO

N  Param.: 15.93

sN Param.: 0.99		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)
C13H14NO6*
 DMSO

N  Param.: 14.94

sN Param.: 0.96		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of triethyl methanetricarboxylate (in DMSO)
C10H15O6*
 DMSO

N  Param.: 15.33

sN Param.: 0.72		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-(acetyl)malonate (in DMSO)
C9H13O5*
 DMSO

N  Param.: 13.83

sN Param.: 0.84		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-(benzoyl)malonate (in DMSO)
C14H15O5*
 DMSO

N  Param.: 13.63

sN Param.: 0.80		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of 5-phenyl Meldrum's acid (in DMSO)
C12H11O4*
 DMSO

N  Param.: 11.54

sN Param.: 0.95		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)
C13H13O5*
 DMSO

N  Param.: 12.35

sN Param.: 0.90		**Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
anion of diethyl 2-(p-anisyl)malonate (in DMSO)
C14H17O5*
 DMSO

N  Param.: 16.73

sN Param.: 0.91		***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
bis(phenylsulfonyl)methanide (in DMSO)
C13H11O4S2*
 DMSO

N  Param.: 15.68

sN Param.: 0.74		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
fluorobis(phenylsulfonyl)methanide (in DMSO)
C13H10FO4S2*
 DMSO

N  Param.: 17.46

sN Param.: 0.73		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
methoxybis(phenylsulfonyl)methanide (in DMSO)
C14H13O5S2*
 DMSO

N  Param.: 17.29

sN Param.: 0.70		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
C7H5O4S2*
 DMSO

N  Param.: 16.06

sN Param.: 0.69		***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)
C7H4FO4S2*
 DMSO

N  Param.: 19.03

sN Param.: 0.58		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
C8H7O5S2*
 DMSO

N  Param.: 17.36

sN Param.: 0.71		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)
C10H11O4S*
 DMSO

N  Param.: 18.81

sN Param.: 0.59		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)
C10H10FO4S*
 DMSO

N  Param.: 20.51

sN Param.: 0.64		***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)
C11H13O5S*
 DMSO

N  Param.: 19.15

sN Param.: 0.59		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
1,3-diethoxy-2-fluoro-1,3-dioxopropan-2-ide (in DMSO)
C7H10FO4*
 DMSO

N  Param.: 20.63

sN Param.: 0.76		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)
C7H10ClO4*
 DMSO

N  Param.: 18.19

sN Param.: 0.74		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
1,2,3-trimethoxy-1,3-dioxopropan-2-ide (in DMSO)
C6H9O5*
 DMSO

N  Param.: 20.08

sN Param.: 0.74		***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616