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