Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
N-(triisopropylsilyl)pyrrole
C13H25NSi *
dichloromethane

N  Param.: 3.12

sN Param.: 0.93
*** Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
Indole
C8H7N *
dichloromethane

N  Param.: 5.55

sN Param.: 1.09
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
N-methylindole
C9H9N *
dichloromethane

N  Param.: 5.75

sN Param.: 1.23
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
(E)-beta-(N-morpholino)styrene
C12H15NO *
dichloromethane

N  Param.: 10.76

sN Param.: 0.87
*** Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
alpha-(N-morpholino)styrene
C12H15NO *
dichloromethane

N  Param.: 9.96

sN Param.: 0.79
*** Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
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[...]
2-(bis(trimethylsiloxy)amino)propene
C9H23NO2Si2 *
dichloromethane

N  Param.: 4.76

sN Param.: 0.86
*** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
2-(bis(tert-butyldimethylsiloxy)amino)propene
C15H35NO2Si2 *
dichloromethane

N  Param.: 4.23

sN Param.: 0.93
*** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester
C12H27NO4Si2 *
dichloromethane

N  Param.: 3.84

sN Param.: 0.87
*** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
1-ethinylcyclohexenyl-Co2(CO)6
*
dichloromethane

N  Param.: -0.44

sN Param.: 1.06
*** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6
*
dichloromethane

N  Param.: -1.11

sN Param.: 0.92
*** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
cyclohepta-1,3,5-trienyl-Fe(CO)3
*
dichloromethane

N  Param.: 3.42

sN Param.: 0.94
*** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
diazomethane
CH2N2 *
dichloromethane

N  Param.: 10.48

sN Param.: 0.78
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
phenyldiazomethane
C7H6N2 *
dichloromethane

N  Param.: 9.35

sN Param.: 0.83
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
(trimethylsilyl)diazomethane
C4H10N2Si *
dichloromethane

N  Param.: 8.97

sN Param.: 0.75
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
diphenyldiazomethane
C13H10N2 *
dichloromethane

N  Param.: 5.29

sN Param.: 0.92
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
ethyl diazoacetate
C4H6N2O2 *
dichloromethane

N  Param.: 4.91

sN Param.: 0.95
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
diazoacetone
C3H4N2O *
dichloromethane

N  Param.: 3.96

sN Param.: 0.91
*** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
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
cyclopentadiene
C5H6 *
dichloromethane

N  Param.: 2.30

sN Param.: 1.06
*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
tetramethylethylene
C6H12 *
dichloromethane

N  Param.: -1.00

sN Param.: 1.40
*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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 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 acetylacetone (in water)
C5H7O2- *
water

N  Param.: 13.73

sN Param.: 0.64
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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 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 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 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 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 3-methyl acetylacetone (in water)
C6H9O2- *
water

N  Param.: 14.33

sN Param.: 0.69
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
1,1-diethoxyethene
C6H12O2 *
dichloromethane

N  Param.: 9.81

sN Param.: 0.81
*** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran
C8H16O2Si *
dichloromethane

N  Param.: 11.50

sN Param.: 0.91
*** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
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 water)
CH2NO2- *
water

N  Param.: 12.06

sN Param.: 0.53
*** 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 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 2-nitropropane (in water)
C3H6NO2- *
water

N  Param.: 10.69

sN Param.: 0.56
*** 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 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 water)
C8H8NO2- *
water

N  Param.: 13.09

sN Param.: 0.50
*** 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 water)
C7H5N2O4- *
water

N  Param.: 13.58

sN Param.: 0.52
*** 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