Mayr's Database of Reactivity Parameters

Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
bromide (in 40% aq MeCN)
Br *
 water-MeCN mix

N  Param.: 12.80

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 50% aq MeCN)
Br *
 water-MeCN mix

N  Param.: 13.80

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in CF3CH2OH)
Br *
 TFE

N  Param.: 11.70

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran
C22H5F15O2Si *
 dichloromethane

N  Param.: 8.16

sN Param.: 0.67		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
5-(triphenylsiloxy)-2,3-dihydrofuran
C22H20O2Si *
 dichloromethane

N  Param.: 11.28

sN Param.: 0.91		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(triphenylsiloxy)cyclopentene
C23H22OSi *
 dichloromethane

N  Param.: 5.76

sN Param.: 1.02		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2,3-dihydrofuran
C4H6O *
 dichloromethane

N  Param.: 4.37

sN Param.: 0.90		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2-(tris(pentafluorophenyl)siloxy)-propene
C21H5F15OSi *
 dichloromethane

N  Param.: 0.58

sN Param.: 0.91		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(tris(pentafluorophenyl)siloxy)-cyclopentene
C23H7F15OSi *
 dichloromethane

N  Param.: 1.38

sN Param.: 0.93		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
nitrite ion (in MeCN)
NO2 *
 MeCN

N  Param.: 17.20

sN Param.: 0.72		 *** Angew. Chem. Int. Ed. 2005, 44, 4623-4626
10.1002/anie.200501274
(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
91% n-propanol/9% MeCN (v/v)
C3H8O *
 nPrOH-MeCN mix

N  Param.: 7.05

sN Param.: 0.80		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
91% propan-2-ol/9% MeCN (v/v)
C3H8O *
 iPrOH-MeCN mix

N  Param.: 6.49

sN Param.: 0.96		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
methanolate (in methanol)
CH3O- *
 MeOH

N  Param.: 15.78

sN Param.: 0.56		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
ethanolate (in ethanol)
C2H5O- *
 EtOH

N  Param.: 15.78

sN Param.: 0.65		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
n-propanolate (in propan-1-ol)
C3H8O- *
 nPrOH

N  Param.: 16.03

sN Param.: 0.70		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
isopropanolate (in propan-2-ol)
C3H8O- *
 iPrOH

N  Param.: 17.03

sN Param.: 0.63		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
methanolate (in 91M9AN)
CH3O- *
 MeOH-MeCN mix

N  Param.: 14.51

sN Param.: 0.68		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
ethanolate (in 91E9AN)
C2H5O- *
 EtOH-MeCN mix

N  Param.: 16.08

sN Param.: 0.62		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
n-propanolate (in 91nPr9AN)
C3H8O- *
 nPrOH-MeCN mix

N  Param.: 16.73

sN Param.: 0.63		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
isopropanolate (in 91iPr9AN)
C3H8O- *
 iPrOH-MeCN mix

N  Param.: 17.71

sN Param.: 0.58		 *** Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
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
azide ion (in 91M9AN)
N3- *
 MeOH-MeCN mix

N  Param.: 14.54

sN Param.: 0.82		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91E9AN)
N3- *
 EtOH-MeCN mix

N  Param.: 16.30

sN Param.: 0.73		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91nPr9AN)
N3- *
 nPrOH-MeCN mix

N  Param.: 16.70

sN Param.: 0.73		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 91iPr9AN)
N3- *
 iPrOH-MeCN mix

N  Param.: 17.07

sN Param.: 0.71		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in DMSO)
N3- *
 DMSO

N  Param.: 20.50

sN Param.: 0.59		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
azide ion (in 45M55AN)
N3- *
 MeOH-MeCN mix

N  Param.: 15.01

sN Param.: 0.80		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
pyrrolidine (in 91M9AN)
C4H9N *
 MeOH-MeCN mix

N  Param.: 15.97

sN Param.: 0.63		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
piperidine (in 91M9AN)
C5H11N *
 MeOH-MeCN mix

N  Param.: 15.63

sN Param.: 0.64		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
morpholine (in 91M9AN)
C4H9NO *
 MeOH-MeCN mix

N  Param.: 15.40

sN Param.: 0.64		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
diethanolamine (in 91M9AN)
C4H11NO2 *
 MeOH-MeCN mix

N  Param.: 13.71

sN Param.: 0.67		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
hydrazine (in 91M9AN)
H4N2 *
 MeOH-MeCN mix

N  Param.: 13.47

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
trimethyl phosphite (in 91M9AN)
C3H9O3P *
 MeOH-MeCN mix

N  Param.: 9.04

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
2,2,2-trifluoroethylamine (in 91M9AN)
C2H4F3N *
 MeOH-MeCN mix

N  Param.: 10.20

sN Param.: 0.92		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
imidazole (in 91M9AN)
C3H4N2 *
 MeOH-MeCN mix

N  Param.: 10.41

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
hydroxylamine (in 91M9AN)
H3NO *
 MeOH-MeCN mix

N  Param.: 12.23

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
ethanolamine (in 91M9AN)
C2H7NO *
 MeOH-MeCN mix

N  Param.: 13.23

sN Param.: 0.65		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
benzylamine (in 91M9AN)
C7H9N *
 MeOH-MeCN mix

N  Param.: 13.46

sN Param.: 0.62		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542