Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(allyl)dicarbonyl(cyclopentadienyl)iron(II)
*
dichloromethane

N  Param.: 6.78

sN Param.: 0.95
*** Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)
*
dichloromethane

N  Param.: 8.45

sN Param.: 0.83
*** Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
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 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 2-nitropropane (in 91M9AN)
C3H6NO2- *
MeOH-MeCN mix

N  Param.: 12.20

sN Param.: 0.71
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 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 (4-nitrophenyl)nitromethane (in 91M9AN)
C7H5N2O4- *
MeOH-MeCN mix

N  Param.: 14.05

sN Param.: 0.72
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
anion of (3-nitrophenyl)nitromethane (in 91M9AN)
C7H5N2O4- *
MeOH-MeCN mix

N  Param.: 14.75

sN Param.: 0.71
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
anion of (4-cyanophenyl)nitromethane (in 91M9AN)
C8H5N2O2- *
MeOH-MeCN mix

N  Param.: 13.92

sN Param.: 0.74
*** Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
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 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 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
5-methoxy-indole
C9H9NO *
dichloromethane

N  Param.: 6.22

sN Param.: 1.12
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-amino-indole
C8H8N2 *
MeCN

N  Param.: 7.22

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-hydroxy-indole
C8H7NO *
MeCN

N  Param.: 6.44

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-methyl-indole
C9H9N *
MeCN

N  Param.: 6.00

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-chloro-indole
C8H6ClN *
MeCN

N  Param.: 4.42

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-bromo-indole
C8H6BrN *
MeCN

N  Param.: 4.38

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-cyano-indole
C9H6N2 *
MeCN

N  Param.: 2.83

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1H-indole-5-carboxylic acid
C9H7NO2 *
MeCN

N  Param.: 3.97

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-methoxy-2-methylindole
C10H11NO *
MeCN

N  Param.: 7.26

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
2,5-dimethylindole
C10H11N *
MeCN

N  Param.: 7.22

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
2-methylindole
C9H9N *
MeCN

N  Param.: 6.91

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
5-chloro-2-methylindole
C9H8ClN *
MeCN

N  Param.: 6.08

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
4-methoxy-indole
C9H9NO *
MeCN

N  Param.: 5.41

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
7-azaindole
C7H6N2 *
MeCN

N  Param.: 3.87

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
tert-butyl isocyanide
C5H9N *
dichloromethane

N  Param.: 5.47

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
benzyl isocyanide
C8H7N *
dichloromethane

N  Param.: 4.90

sN Param.: 0.74
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
2,6-dimethylphenyl isocyanide
C9H9N *
dichloromethane

N  Param.: 4.59

sN Param.: 0.87
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
p-tosylmethyl isocyanide (TosMIC)
C9H9NO2S *
dichloromethane

N  Param.: 3.50

sN Param.: 0.76
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
4-cyanophenyl isocyanide
C8H4N2 *
dichloromethane

N  Param.: 3.57

sN Param.: 0.72
** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
anisole
C7H8O *
dichloromethane

N  Param.: -1.18

sN Param.: 1.20
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)
C8H5F3NO4S- *
MeOH-MeCN mix

N  Param.: 18.24

sN Param.: 0.66
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)
C9H5F3NO2S- *
MeOH-MeCN mix

N  Param.: 19.49

sN Param.: 0.63
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)
C9H5F6O2S- *
MeOH-MeCN mix

N  Param.: 20.72

sN Param.: 0.58
*** 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
10.3998/ark.5550190.[...]
2,5-dimethylpyrrole
C6H9N *
MeCN

N  Param.: 8.01

sN Param.: 0.96
*** Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
1,2,5-trimethylpyrrole
C7H11N *
MeCN

N  Param.: 8.69

sN Param.: 1.07
*** Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
2,4-dimethylpyrrole
C6H9N *
MeCN

N  Param.: 10.67

sN Param.: 0.91
*** Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
3-ethyl-2,4-dimethylpyrrole
C8H13N *
MeCN

N  Param.: 11.63

sN Param.: 0.95
*** Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
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