Mayr's Database of Reactivity Parameters

Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)
C10H10BrO2 *
DMSO

N  Param.: 27.62

sN Param.: 0.53
*** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)
C11H10NO2 *
DMSO

N  Param.: 23.64

sN Param.: 0.65
*** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)
C10H10NO4 *
DMSO

N  Param.: 20.00

sN Param.: 0.71
*** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)
C9H10NO2 *
DMSO

N  Param.: 23.27

sN Param.: 0.70
*** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
potassium trifluoro(1-methyl-1H-indol-2-yl)borate
C9H8BF3KN *
MeCN

N  Param.: 9.55

sN Param.: 1.16
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-5-yl)borate
C9H8BF3KN *
MeCN

N  Param.: 8.77

sN Param.: 1.09
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate
C13H14BF3KNO2 *
MeCN

N  Param.: 6.46

sN Param.: 0.96
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate
C14H16BF3KNO3 *
MeCN

N  Param.: 7.10

sN Param.: 1.18
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate
C13H14BF3KNO2 *
MeCN

N  Param.: 4.06

sN Param.: 0.79
** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
tert-butyl indole-1-carboxylate
C13H15NO2 *
MeCN

N  Param.: 1.68

sN Param.: 1.26
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(furan-2-yl)borate
C4H3BF3KO *
MeCN

N  Param.: 5.99

sN Param.: 0.79
** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(furan-3-yl)borate
C4H3BF3KO *
MeCN

N  Param.: 6.83

sN Param.: 0.93
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(3-methoxy-thiophen-2-yl)borate
C5H5BF3KOS *
MeCN

N  Param.: 7.32

sN Param.: 0.90
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
3-methoxythiophene
C5H6OS *
MeCN

N  Param.: 3.06

sN Param.: 1.19
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
N-methyl-1-phenylmethanimine (in CH2Cl2)
C8H9N *
dichloromethane

N  Param.: 8.60

sN Param.: 0.77
*** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)
C14H13N *
dichloromethane

N  Param.: 7.90

sN Param.: 0.76
** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-phenylpropan-2-imine (in CH2Cl2)
C9H11N *
dichloromethane

N  Param.: 9.53

sN Param.: 0.85
*** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-(phenylmethyl)propan-2-imine (in CH2Cl2)
C10H13N *
dichloromethane

N  Param.: 11.13

sN Param.: 0.73
*** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-phenylcyclohexanimine (in CH2Cl2)
C12H15N *
dichloromethane

N  Param.: 8.80

sN Param.: 1.00
*** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
C30H32N2O *
THF

N  Param.: 15.33

sN Param.: 0.79
*** Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO)
C30H32N2O *
DMSO

N  Param.: 14.40

sN Param.: 0.64
*** Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
C30H34N2O *
THF

N  Param.: 15.92

sN Param.: 0.72
*** Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)
C29H23N3O *
THF

N  Param.: 14.40

sN Param.: 0.66
*** Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)
C29H23N3O *
THF

N  Param.: 16.73

sN Param.: 0.63
** Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2 *
dichloromethane

N  Param.: 6.98

sN Param.: 0.85
*** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2 *
dichloromethane

N  Param.: 19.31

sN Param.: 0.46
*** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2 *
dichloromethane

N  Param.: 7.84

sN Param.: 0.89
*** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2 *
dichloromethane

N  Param.: 17.90

sN Param.: 0.48
*** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C9H12NO2 *
DMSO

N  Param.: 26.71

sN Param.: 0.37
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C11H17N2O *
DMSO

N  Param.: 27.45

sN Param.: 0.38
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)
C7H7N2 *
DMSO

N  Param.: 25.94

sN Param.: 0.42
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)
C8H10NO *
DMSO

N  Param.: 20.24

sN Param.: 0.60
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C13H12NO *
DMSO

N  Param.: 19.46

sN Param.: 0.58
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C15H17N2O *
DMSO

N  Param.: 21.61

sN Param.: 0.58
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C13H11ClNO *
DMSO

N  Param.: 17.98

sN Param.: 0.63
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)
C17H14NO *
DMSO

N  Param.: 19.38

sN Param.: 0.50
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C17H14NO *
DMSO

N  Param.: 20.08

sN Param.: 0.57
*** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
2-(trimethylsilyl)propene
C6H14Si *
dichloromethane

N  Param.: -1.46

sN Param.: 1.05
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-(pentamethyldisilyl)propene
C8H20Si2 *
dichloromethane

N  Param.: -0.26

sN Param.: 0.95
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-(tris(trimethylsilyl)silyl)propene
C12H32Si4 *
dichloromethane

N  Param.: -0.31

sN Param.: 0.99
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
alpha-(trimethylsilyl)styrene
C11H16Si *
dichloromethane

N  Param.: -1.13

sN Param.: 1.46
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
alpha-(pentamethyldisilyl)styrene
C13H22Si2 *
dichloromethane

N  Param.: 0.61

sN Param.: 1.01
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
beta-(trimethylsilyl)styrene
C11H16Si *
dichloromethane

N  Param.: -0.43

sN Param.: 1.06
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-phenyl-allyltrimethylsilane
C12H18Si *
dichloromethane

N  Param.: 5.38

sN Param.: 0.89
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
1-(p-tolyl)-1-(trimethylsilyl)ethene
C12H18Si *
dichloromethane

N  Param.: -0.65

sN Param.: 1.59
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide
C18H19NO2S *
dichloromethane

N  Param.: 5.16

sN Param.: 0.85
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide
C23H21NO3S *
dichloromethane

N  Param.: 4.40

sN Param.: 0.86
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide
C22H19NO2S *
dichloromethane

N  Param.: 3.85

sN Param.: 0.84
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
1-(phenylethynyl)pyrrolidin-2-one
C12H11NO *
dichloromethane

N  Param.: 3.12

sN Param.: 0.85
* Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine
C22H21FN2 *
dichloromethane

N  Param.: 14.57

sN Param.: 0.75
*** Eur. J. Org. Chem. 2014, , 1202-1211
10.1002/ejoc.201301730