Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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-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-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 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 malonate (in water)
C7H11O4- *
water

N  Param.: 16.15

sN Param.: 0.66
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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 methylmalonate (in water)
C8H13O4- *
water

N  Param.: 17.68

sN Param.: 0.50
* J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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 dimedone (in water)
C8H11O2- *
water

N  Param.: 11.77

sN Param.: 0.63
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of dimethyl malonate (in 91M9AN)
C5H7O4- *
MeOH-MeCN mix

N  Param.: 18.24

sN Param.: 0.64
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 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 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 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 acetylacetate (in water)
C6H9O3- *
water

N  Param.: 15.99

sN Param.: 0.62
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of ethyl cyanoacetate (in 91M9AN)
C5H6NO2- *
MeOH-MeCN mix

N  Param.: 18.59

sN Param.: 0.65
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 cyanoacetate (in water)
C5H6NO2- *
water

N  Param.: 15.57

sN Param.: 0.58
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of malononitrile (in 91M9AN)
C3HN2- *
MeOH-MeCN mix

N  Param.: 18.21

sN Param.: 0.69
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 malononitrile (in water)
C3HN2- *
water

N  Param.: 19.50

sN Param.: 0.55
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of Meldrum's acid (in water)
C6H7O4- *
water

N  Param.: 12.06

sN Param.: 0.66
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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 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 nitroethane (in 91M9AN)
C2H4NO2- *
MeOH-MeCN mix

N  Param.: 13.41

sN Param.: 0.67
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
anion of nitroethane (in DMF)
C2H4NO2- *
DMF

N  Param.: 22.21

sN Param.: 0.48
*** Chem. Eur. J. 2008, 14, 6108-6118
10.1002/chem.200800329
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 nitroethane (in water)
C2H4NO2- *
water

N  Param.: 11.25

sN Param.: 0.52
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of nitromethane (in 91M9AN)
CH2NO2- *
MeOH-MeCN mix

N  Param.: 14.02

sN Param.: 0.61
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 nitromethane (in water)
CH2NO2- *
water

N  Param.: 12.06

sN Param.: 0.53
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of p-tolylnitromethane (in 91M9AN)
C8H8NO2- *
MeOH-MeCN mix

N  Param.: 13.58

sN Param.: 0.64
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 p-tolylnitromethane (in water)
C8H8NO2- *
water

N  Param.: 13.09

sN Param.: 0.50
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of phenylnitromethane (in 91M9AN)
C7H6NO2- *
MeOH-MeCN mix

N  Param.: 12.51

sN Param.: 0.67
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 phenylnitromethane (in H2O)
C7H6NO2- *
water

N  Param.: 12.05

sN Param.: 0.53
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
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
anisole
C7H8O *
dichloromethane

N  Param.: -1.18

sN Param.: 1.20
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
azulene
C10H8 *
MeCN

N  Param.: 6.66

sN Param.: 1.02
*** Eur. J. Org. Chem. 2009, , 1202-1206
10.1002/ejoc.200801099
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
benzyl (1-phenylvinyl)carbamate
C16H15NO2 *
MeCN

N  Param.: 6.21

sN Param.: 0.87
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
benzyl isocyanide
C8H7N *
dichloromethane

N  Param.: 4.90

sN Param.: 0.74
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
beta-(trimethylsilyl)styrene
C11H16Si *
dichloromethane

N  Param.: -0.43

sN Param.: 1.06
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
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.[...]
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
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
buta-1,3-diene
C4H6 *
dichloromethane

N  Param.: -0.87

sN Param.: 1.00
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
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