Mayr's Database of Reactivity Parameters

Carbanions in DMSO

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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 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 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 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 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 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 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 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 3-methyl acetylacetone (in DMSO)
C6H9O2-*
DMSO

N  Param.: 18.38

sN Param.: 0.72
***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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 2-nitropropane (in DMSO)
C3H6NO2-*
DMSO

N  Param.: 20.61

sN Param.: 0.69
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
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 (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-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4-*
DMSO

N  Param.: 18.06

sN Param.: 0.71
***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
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
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-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-(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
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 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
bis(4-nitrophenyl)methanide (in DMSO)
C13H9N2O4-*
DMSO

N  Param.: 19.92

sN Param.: 0.67
***ARKIVOC 2008, (x), 37-53
http://www.arkat-usa[...]
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
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)
C9H5F3N-*
DMSO

N  Param.: 27.28

sN Param.: 0.50
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
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
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 2-phenyl-propionitrile (in DMSO)
C9H8N-*
DMSO

N  Param.: 28.95

sN Param.: 0.58
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 2-(4-CN-C6H4)propionitrile (in DMSO)
C10H7N2-*
DMSO

N  Param.: 25.35

sN Param.: 0.56
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO)
C9H7N2O2-*
DMSO

N  Param.: 19.61

sN Param.: 0.60
***J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
(EtO)2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.23

sN Param.: 0.65
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(EtO)2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.57

sN Param.: 0.66
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
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
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
2-PhCH(-)CO2Et (in DMSO)
C10H11O2*
DMSO

N  Param.: 27.54

sN Param.: 0.57
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)
C10H10ClO2*
DMSO

N  Param.: 27.57

sN Param.: 0.53
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)
C10H10BrO2*
DMSO

N  Param.: 27.62

sN Param.: 0.53
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)
C11H10NO2*
DMSO

N  Param.: 23.64

sN Param.: 0.65
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)
C10H10NO4*
DMSO

N  Param.: 20.00

sN Param.: 0.71
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)
C9H10NO2*
DMSO

N  Param.: 23.27

sN Param.: 0.70
***Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
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
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
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
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
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 1,2-diphenylethanone (in DMSO)
C14H11O*
DMSO

N  Param.: 23.15

sN Param.: 0.60
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500