Mayr's Database of Reactivity Parameters

Carbanions in DMSO

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
sodium indenide (in DMSO)
C9H7Na*
DMSO

N  Param.: 23.74

sN Param.: 0.71
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
potassium indenide (in DMSO)
C9H7K*
DMSO

N  Param.: 24.16

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
Ph2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.20

sN Param.: 0.69
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.69

sN Param.: 0.72
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
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
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
MeSO-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 20.61

sN Param.: 0.64
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
lithium indenide (in DMSO)
C9H7Li*
DMSO

N  Param.: 23.66

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
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
cyano((diphenylmethylene)amino)methanide
*
DMSO

N  Param.: 29.50

sN Param.: 0.50
*Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
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
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-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-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
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
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
bis(4-nitrophenyl)methanide (in DMSO)
C13H9N2O4-*
DMSO

N  Param.: 19.92

sN Param.: 0.67
***ARKIVOC 2008, (x), 37-53
10.3998/ark.5550190.[...]
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
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 phenylnitromethane (in DMSO)
C7H6NO2-*
DMSO

N  Param.: 18.29

sN Param.: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of p-tolylnitromethane (in DMSO)
C8H8NO2-*
DMSO

N  Param.: 18.31

sN Param.: 0.76
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of nitromethane (in DMSO)
CH2NO2-*
DMSO

N  Param.: 20.71

sN Param.: 0.60
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of nitroethane (in DMSO)
C2H4NO2*
DMSO

N  Param.: 21.54

sN Param.: 0.62
***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO)
C13H16NO2*
DMSO

N  Param.: 19.28

sN Param.: 0.65
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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 malononitrile (in DMSO)
C3HN2*
DMSO

N  Param.: 19.36

sN Param.: 0.67
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of ethyl cyanoacetate (in DMSO)
C5H6NO2*
DMSO

N  Param.: 19.62

sN Param.: 0.67
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of ethyl acetylacetate (in DMSO)
C6H9O3*
DMSO

N  Param.: 18.82

sN Param.: 0.69
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
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 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 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 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 diethyl methylmalonate (in DMSO)
C8H13O4-*
DMSO

N  Param.: 21.13

sN Param.: 0.68
***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of diethyl malonate (in DMSO)
C7H11O4*
DMSO

N  Param.: 20.22

sN Param.: 0.65
***Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
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-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-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-(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 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-(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 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-(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 benzyl trifluoromethyl sulfone (in DMSO)
C8H6F3O2S-*
DMSO

N  Param.: 18.67

sN Param.: 0.68
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
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[...]
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 4-nitrobenzyl-CN (in DMSO)
C8H5N2O2-*
DMSO

N  Param.: 19.67

sN Param.: 0.68
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
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
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO)
C9H8F3O2S-*
DMSO

N  Param.: 19.35

sN Param.: 0.67
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-cyanobenzyl-CN (in DMSO)
C9H5N2-*
DMSO

N  Param.: 25.11

sN Param.: 0.54
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x