Mayr's Database of Reactivity Parameters

Carbanions in DMSO

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles » Carbanions
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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
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
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
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-NO2-C6H4)CH2SO2Ph (in DMSO)
C13H10NO4S-*
 DMSO

N  Param.: 18.50

sN Param.: 0.75		***Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)
C14H10NO2S-*
 DMSO

N  Param.: 22.60

sN Param.: 0.57		***Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)
C14H10F3O2S-*
 DMSO

N  Param.: 24.30

sN Param.: 0.51		***Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
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[...]