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)
tetraethylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -1.90

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
tetrapropylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -0.50

sN Param.: 1.13		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
tetra-sec.butylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -1.10

sN Param.: 1.15		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-chlorophenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -1.80

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
trimethyl(phenethyl)stannane
*
 1,2-dichloroethane

N  Param.: -1.10

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.80

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
trimethyl(4-methylphenethyl)stannane
*
 1,2-dichloroethane

N  Param.: -0.50

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-(tert-butyl)phenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.30

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-methoxyphenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: 0.20

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
p-nitrobenzoate (in acetone)
*
 acetone

N  Param.: 18.74

sN Param.: 0.68		 *** J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
3,5-dinitrobenzoate (in acetone)
*
 acetone

N  Param.: 18.80

sN Param.: 0.62		 ** J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
acetate (in 90A10W)
*
 aq acetone

N  Param.: 12.71

sN Param.: 0.68		 *** J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
acetate (in 80A20W)
*
 aq acetone

N  Param.: 12.50

sN Param.: 0.60		 ** J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
benzoate (in 90AN10W)
*
 aq MeCN

N  Param.: 11.30

sN Param.: 0.72		 ** J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
2-(1-azidovinyl)naphthalene (in Cyrene)
C12H9N3 *
 Cyrene (TM)

N  Param.: 6.00

sN Param.: 0.90		 *** Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
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
triphenylphosphane
C18H15P *
 dichloromethane

N  Param.: 14.33

sN Param.: 0.65		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
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
methylenecycloheptane
C8H14 *
 dichloromethane

N  Param.: 2.24

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclooctane
C9H16 *
 dichloromethane

N  Param.: 3.16

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclononane
C10H18 *
 dichloromethane

N  Param.: 2.57

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclodecane
C11H20 *
 dichloromethane

N  Param.: 2.82

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecycloundecane
C12H22 *
 dichloromethane

N  Param.: 2.33

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclododecane
C13H24 *
 dichloromethane

N  Param.: 1.52

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclopentadecane
C16H30 *
 dichloromethane

N  Param.: 1.69

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