Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
6-(4-dimethylamino-phenyl)fulvene
C14H15N *
MeCN

N  Param.: 6.72

sN Param.: 0.87
*** Eur. J. Org. Chem. 2009, , 1202-1206
10.1002/ejoc.200801099
6-(julolidin-9-yl)fulvene
C18H19N *
MeCN

N  Param.: 7.79

sN Param.: 1.06
*** Eur. J. Org. Chem. 2009, , 1202-1206
10.1002/ejoc.200801099
Ph3P=CH-CO2Et
*
dichloromethane

N  Param.: 12.79

sN Param.: 0.77
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 12.21

sN Param.: 0.62
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=C(CH3)-CO2Et
*
dichloromethane

N  Param.: 13.09

sN Param.: 0.73
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CN
*
dichloromethane

N  Param.: 12.29

sN Param.: 0.75
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-COPh
*
dichloromethane

N  Param.: 9.54

sN Param.: 0.97
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(EtO)2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.23

sN Param.: 0.65
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(EtO)2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.57

sN Param.: 0.66
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.20

sN Param.: 0.69
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.69

sN Param.: 0.72
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(4-Br-C6H4)-(CO)-CH=SMe2
*
dichloromethane

N  Param.: 11.95

sN Param.: 0.76
*** Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
Me2S=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 15.85

sN Param.: 0.61
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
Me2S=CH-CN (in DMSO)
*
DMSO

N  Param.: 16.23

sN Param.: 0.60
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
MeSO2-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.66
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
MeSO-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 20.61

sN Param.: 0.64
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
(cyclohexen-1-yl)prolinate (in MeCN)
*
MeCN

N  Param.: 18.86

sN Param.: 0.70
*** Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
1-(N-pyrrolidino)cyclohexene (in MeCN)
*
MeCN

N  Param.: 16.42

sN Param.: 0.70
*** Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
methyl (cyclohexen-1-yl)prolinate (in MeCN)
*
MeCN

N  Param.: 14.96

sN Param.: 0.68
*** Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 13.78

sN Param.: 0.72
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(C6H5)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 13.95

sN Param.: 0.69
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 14.48

sN Param.: 0.71
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 15.68

sN Param.: 0.65
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S=CH(p-NO2-C6H4) (in DMSO)
*
DMSO

N  Param.: 18.42

sN Param.: 0.65
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S=CH(4-CN-C6H4) (in DMSO)
*
DMSO

N  Param.: 21.07

sN Param.: 0.68
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S(O)=CH2 (in DMSO)
*
DMSO

N  Param.: 21.29

sN Param.: 0.47
*** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
allyltris(trimethylsilyl)silane
*
dichloromethane

N  Param.: 1.95

sN Param.: 0.98
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
(2-methylallyl)tris(trimethylsilyl)silane
*
dichloromethane

N  Param.: 4.63

sN Param.: 0.87
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
2-(tris(trimethylsilyl)siloxy)propene
*
dichloromethane

N  Param.: 6.04

sN Param.: 0.82
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
1-(tris(trimethylsilyl)siloxy)cyclohexene
*
dichloromethane

N  Param.: 5.07

sN Param.: 0.91
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
(tris(trimethylsilyl)siloxy)ethene
*
dichloromethane

N  Param.: 4.01

sN Param.: 0.83
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)
C21H24N2 *
THF

N  Param.: 21.72

sN Param.: 0.45
*** Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)
C21H26N2 *
THF

N  Param.: 23.35

sN Param.: 0.40
*** Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)
C20H15N3 *
THF

N  Param.: 14.07

sN Param.: 0.84
*** Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
1-(N-piperidino)cyclohexene (in MeCN)
*
MeCN

N  Param.: 14.02

sN Param.: 0.76
*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)
*
MeCN

N  Param.: 12.34

sN Param.: 0.72
*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)
*
MeCN

N  Param.: 10.52

sN Param.: 0.78
*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)
*
MeCN

N  Param.: 9.11

sN Param.: 0.88
*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
(5-methyl-furan-2-yl) pinacol boronate
*
MeCN

N  Param.: 2.90

sN Param.: 0.98
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
(5-methyl-furan-2-yl) MDA boronate
*
MeCN

N  Param.: 6.38

sN Param.: 0.86
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
(5-methyl-furan-2-yl) trifluoroborate
*
MeCN

N  Param.: 7.66

sN Param.: 1.04
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
tetrakis(5-methyl-furan-2-yl)borate
*
MeCN

N  Param.: 9.09

sN Param.: 1.12
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate
*
MeCN

N  Param.: 12.55

sN Param.: 0.92
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
N-(1-phenylvinyl)acetamide
C10H11NO *
MeCN

N  Param.: 5.73

sN Param.: 0.97
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(4-methoxyphenyl)vinyl)acetamide
C11H13NO2 *
MeCN

N  Param.: 7.06

sN Param.: 0.85
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(4-chlorophenyl)vinyl)acetamide
C10H10ClNO *
MeCN

N  Param.: 5.60

sN Param.: 1.00
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
benzyl (1-phenylvinyl)carbamate
C16H15NO2 *
MeCN

N  Param.: 6.21

sN Param.: 0.87
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(naphthalen-2-yl)vinyl)acetamide
C14H13NO *
MeCN

N  Param.: 6.28

sN Param.: 0.95
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(3,4-dihydronaphthalen-1-yl)acetamide
C12H13NO *
MeCN

N  Param.: 4.91

sN Param.: 0.87
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(cyclohex-1-en-1-yl)acetamide
C8H13NO *
MeCN

N  Param.: 5.64

sN Param.: 0.79
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519