Mayr's Database of Reactivity Parameters

Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
toluene
C7H8*
dichloromethane

N  Param.: -4.36

sN Param.: 1.77
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
m-xylene
C8H10*
dichloromethane

N  Param.: -3.57

sN Param.: 2.08
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(E)-propenylbenzene
C9H10*
dichloromethane

N  Param.: -0.49

sN Param.: 1.18
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2-methylthiophene
C5H6S*
dichloromethane

N  Param.: 1.35

sN Param.: 0.99
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
styrene
C8H8*
dichloromethane

N  Param.: 0.78

sN Param.: 0.95
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1,3-dimethoxybenzene
C8H10O2*
dichloromethane

N  Param.: 2.48

sN Param.: 1.09
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
allyltrimethylsilane
C6H14Si*
dichloromethane

N  Param.: 1.68

sN Param.: 1.00
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
allyltriphenylstannane
C21H20Sn*
dichloromethane

N  Param.: 3.09

sN Param.: 0.90
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(2-methylallyl)trimethylsilane
C7H16Si*
dichloromethane

N  Param.: 4.41

sN Param.: 0.96
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
allyltributylstannane
C15H32Sn*
dichloromethane

N  Param.: 5.46

sN Param.: 0.89
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(2-methylallyl)tributylstannane
C16H34Sn*
dichloromethane

N  Param.: 7.48

sN Param.: 0.89
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
Danishefskys diene
C8H16O2Si*
dichloromethane

N  Param.: 8.57

sN Param.: 0.84
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran
C8H16O2Si*
dichloromethane

N  Param.: 10.61

sN Param.: 0.86
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
5-(trimethylsiloxy)-2,3-dihydrofuran
C7H14O2Si*
dichloromethane

N  Param.: 12.56

sN Param.: 0.70
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
methylenecyclopentane
C6H10*
dichloromethane

N  Param.: 2.82

sN Param.: 0.90
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methylfuran
C5H6O*
dichloromethane

N  Param.: 3.61

sN Param.: 1.11
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-methylpyrrole
C5H7N*
dichloromethane

N  Param.: 5.85

sN Param.: 1.03
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(trimethylsiloxy)cyclohexene
C9H18OSi*
dichloromethane

N  Param.: 5.21

sN Param.: 1.00
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(trimethylsiloxy)propene
C6H14OSi*
dichloromethane

N  Param.: 5.41

sN Param.: 0.91
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-phenyl-1-(trimethylsiloxy)ethene
C11H16OSi*
dichloromethane

N  Param.: 6.22

sN Param.: 0.96
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(trimethylsiloxy)cyclopentene
C8H16OSi*
dichloromethane

N  Param.: 6.57

sN Param.: 0.93
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-phenoxy-1-(trimethylsiloxy)ethene
C11H16O2Si*
dichloromethane

N  Param.: 8.23

sN Param.: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(N-morpholino)cyclohexene
C10H17NO*
dichloromethane

N  Param.: 11.40

sN Param.: 0.83
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-(N-piperidino)cyclohexene
C11H19N*
dichloromethane

N  Param.: 13.36

sN Param.: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(Z)-but-2-ene
C4H8*
dichloromethane

N  Param.: -2.44

sN Param.: 1.09
**J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
allyltriphenylsilane
C21H20Si*
dichloromethane

N  Param.: -0.13

sN Param.: 1.21
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
3-methylanisole
C8H10O*
dichloromethane

N  Param.: 0.13

sN Param.: 1.27
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
phenylacetylene
C8H6*
dichloromethane

N  Param.: -0.04

sN Param.: 0.77
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
(triisopropylsiloxy)ethene
C11H24OSi*
dichloromethane

N  Param.: 3.44

sN Param.: 0.94
**J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(2-methylallyl)triphenylsilane
C22H22Si*
dichloromethane

N  Param.: 4.17

sN Param.: 0.79
**J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-(triisopropylsiloxy)propene
C12H26OSi*
dichloromethane

N  Param.: 5.38

sN Param.: 0.85
**J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
phenylsilane
C6H8Si*
dichloromethane

N  Param.: 0.06

sN Param.: 0.71
***Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
triphenylsilane
C18H16Si*
dichloromethane

N  Param.: 2.65

sN Param.: 0.72
***Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dimethyl(phenyl)silane
C8H12Si*
dichloromethane

N  Param.: 3.55

sN Param.: 0.75
***Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
triethylsilane
C6H16Si*
dichloromethane

N  Param.: 3.58

sN Param.: 0.70
***J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
triphenylgermane
C18H16Ge*
dichloromethane

N  Param.: 3.99

sN Param.: 0.62
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tributylsilane
C12H28Si*
dichloromethane

N  Param.: 3.99

sN Param.: 0.73
***Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
triphenylstannane
C18H16Sn*
dichloromethane

N  Param.: 5.64

sN Param.: 0.59
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tributylgermane
C12H28Ge*
dichloromethane

N  Param.: 5.92

sN Param.: 0.73
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
borane-triethylamine-complex
C6H18BN*
dichloromethane

N  Param.: 8.90

sN Param.: 0.75
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tributylstannane
C12H28Sn*
dichloromethane

N  Param.: 9.96

sN Param.: 0.55
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
cycloheptatriene
C7H8*
dichloromethane

N  Param.: 0.52

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1-(N-pyrrolidino)cyclopentene
C9H15N*
dichloromethane

N  Param.: 15.91

sN Param.: 0.86
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-(N-piperidino)cyclopentene
C10H17N*
dichloromethane

N  Param.: 15.06

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-(N-pyrrolidino)cyclohexene
C10H17N*
dichloromethane

N  Param.: 14.91

sN Param.: 0.86
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-(N-morpholino)cyclopentene
C9H15NO*
dichloromethane

N  Param.: 13.41

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-(phenylmethylamino)cyclopentene
C12H15N*
dichloromethane

N  Param.: 12.90

sN Param.: 0.79
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-(phenylmethylamino)cyclohexene
C13H17N*
dichloromethane

N  Param.: 10.73

sN Param.: 0.81
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
morpholinoisobutylene
C8H15NO*
dichloromethane

N  Param.: 10.04

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
N-vinylcarbazole
C14H11N*
dichloromethane

N  Param.: 5.02

sN Param.: 0.94
**Macromolecules 2002, 35, 5454-5458
10.1021/ma020306l
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
1,2-dimethylindole
C10H11N*
dichloromethane

N  Param.: 6.54

sN Param.: 1.10
*J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1-(1-cyclohexenyl)-4-methylpiperazine
C11H20N2*
dichloromethane

N  Param.: 12.51

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
(Z)-1-(N-morpholino)propene
C7H13NO*
dichloromethane

N  Param.: 12.26

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
(E)-1-(N-morpholino)propene
C7H13NO*
dichloromethane

N  Param.: 12.06

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1-methyl-4-(N-morpholino)tetrahydropyridine
C10H18N2O*
dichloromethane

N  Param.: 12.03

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
(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
ethyl (E)-3-(dimethylamino)acrylate
C7H13NO2*
dichloromethane

N  Param.: 9.43

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
ethyl (E)-3-(N-morpholino)acrylate
C9H15NO3*
dichloromethane

N  Param.: 8.52

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
1,4-cyclohexadiene
C6H8*
dichloromethane

N  Param.: 0.09

sN Param.: 0.98
***J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,4-dihydronaphthalene
C10H10*
dichloromethane

N  Param.: -0.07

sN Param.: 1.03
***J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
9,10-dihydroanthracene
C14H12*
dichloromethane

N  Param.: -0.86

sN Param.: 0.92
***J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
(E,E)-2,5-heptadiene
C7H12*
dichloromethane

N  Param.: -0.74

sN Param.: 0.99
***J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
3-propylcyclopentene
C8H14*
dichloromethane

N  Param.: -0.88

sN Param.: 0.94
***J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
xanthene
C13H10O*
dichloromethane

N  Param.: 0.64

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
4-methyl-2,5-heptadiene
C8H14*
dichloromethane

N  Param.: -0.73

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
3-methyl-1,4-pentadiene
C6H10*
dichloromethane

N  Param.: -3.08

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,4-pentadiene
C5H8*
dichloromethane

N  Param.: -2.99

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
p-cymene
C10H14*
dichloromethane

N  Param.: -2.80

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
allylbenzene
C9H10*
dichloromethane

N  Param.: -4.12

sN Param.: 0.97
*J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
pyrrole
C4H5N*
dichloromethane

N  Param.: 4.63

sN Param.: 1.00
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
H2O (in water)
H2O*
water

N  Param.: 5.20

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
OH- (in 50/50 water/MeCN)
HO*
water-MeCN mix

N  Param.: 10.19

sN Param.: 0.62
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
OH- (in water)
HO*
water

N  Param.: 10.47

sN Param.: 0.61
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
semicarbazide (in water)
CH5N3O*
water

N  Param.: 11.05

sN Param.: 0.52
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
hydroxylamine (in water)
H3NO*
water

N  Param.: 11.41

sN Param.: 0.55
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,2-trifluoroethylamine (in DMSO)
C2H4F3N*
DMSO

N  Param.: 12.15

sN Param.: 0.65
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,2-trifluoroethanolate (in water)
C2H2F3O*
water

N  Param.: 12.66

sN Param.: 0.59
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in water)
C3H9N*
water

N  Param.: 13.33

sN Param.: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ethyl glycinate (in DMSO)
C4H9NO2*
DMSO

N  Param.: 14.30

sN Param.: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
HOO- (in water)
HO2*
water

N  Param.: 15.40

sN Param.: 0.55
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in DMSO)
C3H9N*
DMSO

N  Param.: 15.70

sN Param.: 0.64
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
SO3(2-) (in water)
O3S*
water

N  Param.: 16.83

sN Param.: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
morpholine (in DMSO)
C4H9NO*
DMSO

N  Param.: 16.96

sN Param.: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
piperidine (in DMSO)
C5H11N*
DMSO

N  Param.: 17.19

sN Param.: 0.71
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2-sulfidoacetate (in water)
C2H2O2S*
water

N  Param.: 22.62

sN Param.: 0.43
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
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[...]
triphenylphosphane
C18H15P*
dichloromethane

N  Param.: 14.33

sN Param.: 0.65
***Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
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[...]
methylenecyclopropane
C4H6*
dichloromethane

N  Param.: -0.47

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclobutane
C5H8*
dichloromethane

N  Param.: 1.65

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclohexane
C7H12*
dichloromethane

N  Param.: 1.16

sN Param.: 1.04
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b