Mayr's Database of Reactivity Parameters

Carbanions in DMSO

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C13H12NO6*
DMSO

N  Param.: 12.02

sN Param.: 1.17
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
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-(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
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C14H12NO4*
DMSO

N  Param.: 13.79

sN Param.: 0.86
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
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 Meldrums acid (in DMSO)
C6H7O4*
DMSO

N  Param.: 13.91

sN Param.: 0.86
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of 2-nitro-1-phenylethan-1-one (in DMSO)
C8H6NO3*
DMSO

N  Param.: 13.91

sN Param.: 0.76
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)
C6H7O3*
DMSO

N  Param.: 14.46

sN Param.: 0.91
***Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C15H18NO4*
DMSO

N  Param.: 14.48

sN Param.: 0.86
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)
C8H5F3NO4S-*
DMSO

N  Param.: 14.49

sN Param.: 0.86
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
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-(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 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
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C13H13O4*
DMSO

N  Param.: 15.02

sN Param.: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
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
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C14H15O5*
DMSO

N  Param.: 15.13

sN Param.: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
anion of ethyl 2-nitroacetate (in DMSO)
C4H6NO4*
DMSO

N  Param.: 15.24

sN Param.: 0.74
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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 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
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
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
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 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-phenylmalonate (in DMSO)
C13H16O4*
DMSO

N  Param.: 15.93

sN Param.: 0.99
***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 1-phenylbutane-1,3-dione (in DMSO)
C10H9O2*
DMSO

N  Param.: 16.03

sN Param.: 0.86
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
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
anion of dimedone (in DMSO)
C8H11O2*
DMSO

N  Param.: 16.27

sN Param.: 0.77
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)
C9H5F3NO2S-*
DMSO

N  Param.: 16.28

sN Param.: 0.75
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of (4-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4-*
DMSO

N  Param.: 16.29

sN Param.: 0.75
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)
C9H6NO*
DMSO

N  Param.: 16.55

sN Param.: 0.78
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
anion of (4-cyanophenyl)nitromethane (in DMSO)
C8H5N2O2-*
DMSO

N  Param.: 16.96

sN Param.: 0.73
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)
C7H9O3*
DMSO

N  Param.: 17.00

sN Param.: 0.74
***Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)
C14H11O3S*
DMSO

N  Param.: 17.19

sN Param.: 0.56
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)
C9H5F6O2S-*
DMSO

N  Param.: 17.33

sN Param.: 0.74
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
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
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)
C15H11O2*
DMSO

N  Param.: 17.46

sN Param.: 0.65
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
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
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)
C11H11O3*
DMSO

N  Param.: 17.52

sN Param.: 0.74
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of acetylacetone (in DMSO)
C5H7O2*
DMSO

N  Param.: 17.64

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
MeSO2-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.66
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
anion of (3-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4-*
DMSO

N  Param.: 18.06

sN Param.: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
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
anion of phenylnitromethane (in DMSO)
C7H6NO2-*
DMSO

N  Param.: 18.29

sN Param.: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j