Mayr's Database of Reactivity Parameters

Electrophiles

For reactivities of structurally related compounds go to: Electrophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
N-methyl maleimide
C5H7NO2 *
 DMSO

E Param.: -14.07

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
fumaronitrile
C4H2N2 *
 DMSO

E Param.: -15.71

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
diethyl fumarate
C8H12O4 *
 DMSO

E Param.: -17.79

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
diethyl maleate
C8H12O4 *
 DMSO

E Param.: -19.49

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
ethenesulfonyl fluoride (ESF)
*
 DMSO

E Param.: -12.09

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
2-phenylethene-1-sulfonyl fluoride
C8H7FO2S *
 DMSO

E Param.: -16.63

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
(E)-4-phenylbut-3-en-2-one (in DMSO)
C10H10O *
 DMSO

E Param.: -23.01

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
cinnamonitrile (in DMSO)
C9H7N *
 DMSO

E Param.: -24.60

 * J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
methyl prop-2-enoate (in DMSO)
C4H6O2 *
 DMSO

E Param.: -18.84

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl prop-2-enoate (in DMSO)
C5H8O2 *
 DMSO

E Param.: -19.07

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
tert-butyl prop-2-enoate (in DMSO)
C7H12O2 *
 DMSO

E Param.: -20.22

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
N,N-dimethylprop-2-enamide (in DMSO)
C5H9NO *
 DMSO

E Param.: -23.54

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethenylsulfonylbenzene (in DMSO)
C8H8O2S *
 DMSO

E Param.: -18.36

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
acrylonitrile (in DMSO)
C3H3N *
 DMSO

E Param.: -19.05

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
but-3-en-2-one (in DMSO)
C4H6O *
 DMSO

E Param.: -16.76

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
1-phenylprop-2-en-1-one (in DMSO)
C9H8O *
 DMSO

E Param.: -15.25

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl 2-methylprop-2-enoate (in DMSO)
C6H10O2 *
 DMSO

E Param.: -22.77

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl (E)-but-2-enoate (in DMSO)
C6H10O2 *
 DMSO

E Param.: -23.59

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ethyl cinnamate (in DMSO)
C11H12O2 *
 DMSO

E Param.: -24.52

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-1-methyl-4-(styrylsulfonyl)benzene (in DMSO)
C15H14O2S *
 DMSO

E Param.: -24.69

 ** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium
C19H12F5N2O *
 DMSO

E Param.: -10.09

 *** Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium
C17H21N2O *
 DMSO

E Param.: -11.80

 *** Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium
C22H23N2O *
 DMSO

E Param.: -11.48

 *** Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium
C20H19N2O2 *
 DMSO

E Param.: -11.79

 *** Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium
C21H21N2O3 *
 DMSO

E Param.: -12.02

 *** Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
cyclobutanone (in DMSO)
C4H6O *
 DMSO

E Param.: -17.50

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
cyclopentanone (in DMSO)
C5H8O *
 DMSO

E Param.: -21.00

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
cyclohexanone (in DMSO)
C6H10O *
 DMSO

E Param.: -19.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
cycloheptanone (in DMSO)
C7H12O *
 DMSO

E Param.: -22.10

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
1-methylpiperidin-4-one (in DMSO)
C6H11NO *
 DMSO

E Param.: -18.40

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
oxan-4-one (in DMSO)
C5H8O2 *
 DMSO

E Param.: -17.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
thian-4-one (in DMSO)
C5H8OS *
 DMSO

E Param.: -16.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
1,4-dioxaspiro[4.5]decan-8-one (in DMSO)
C8H12O3 *
 DMSO

E Param.: -18.20

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
pentan-2-one (in DMSO)
C5H10O *
 DMSO

E Param.: -22.30

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
1-methylsulfanylpropan-2-one (in DMSO)
C4H8OS *
 DMSO

E Param.: -15.60

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
3-methylcyclopentenone
C6H8O *
 DMSO

E Param.: -28.90

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
2-methylcyclopentenone
C6H8O *
 DMSO

E Param.: -22.10

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclopentenone
C5H6O *
 DMSO

E Param.: -20.60

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
furan-2(5H)-one
C4H4O2 *
 DMSO

E Param.: -20.70

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
2-methylcyclohexenone
C7H10O *
 DMSO

E Param.: -27.50

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclohexenone
C6H8O *
 DMSO

E Param.: -22.10

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
dihydro-2H-pyran-2-one
C5H6O2 *
 DMSO

E Param.: -21.80

 ** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
3-methylenetetrahydropyran-2-one
C6H8O2 *
 DMSO

E Param.: -19.50

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
3-methylenedihydrofuranone
C5H6O2 *
 DMSO

E Param.: -19.40

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
(E)-2,6-di-tert-butyl-4-(3-phenylallylidene)cyclohexa-2,5-dien-1-one
C23H28O *
 DMSO

E Param.: -17.00

 *** Org. Lett. 2020, 22, 2182-2186
10.1021/acs.orglett.[...]
E)-2,6-di-tert-butyl-4-(3-(4-chlorophenyl)allylidene)cyclohexa-2,5-dien-1-one
C23H27ClO *
 DMSO

E Param.: -16.84

 *** Org. Lett. 2020, 22, 2182-2186
10.1021/acs.orglett.[...]
(E)-2,6-di-tert-butyl-4-(3-(4-nitrophenyl)allylidene)cyclohexa-2,5-dien-1-one
C23H27NO3 *
 DMSO

E Param.: -16.25

 *** Org. Lett. 2020, 22, 2182-2186
10.1021/acs.orglett.[...]
(E)-2,6-di-tert-butyl-4-(3-(4-methoxyphenyl)allylidene)cyclohexa-2,5-dien-1-one
C24H30O2 *
 DMSO

E Param.: -17.42

 *** Org. Lett. 2020, 22, 2182-2186
10.1021/acs.orglett.[...]
2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one
C16H21F3O *
 DMSO

E Param.: -11.68

 *** Eur. J. Org. Chem. 2020, , 3812-3817
10.1002/ejoc.202000295
phenyl isothiocyanate
C7H5NS *
 DMSO

E Param.: -18.15

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
p-nitrophenyl isothiocyanate
C7H4N2O2S *
 DMSO

E Param.: -15.89

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
diphenylcarbodiimide
C13H10N2 *
 DMSO

E Param.: -20.14

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
carbon disulfide
CS2 *
 DMSO

E Param.: -17.70

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
3-methylcyclohexenone
C7H10O *
 DMSO

E Param.: -29.60

 * Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cycloheptenone
C7H10O *
 DMSO

E Param.: -22.00

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
MacMillan-iminium ion (1st generation)
C22H25N2O+ *
 MeCN

E Param.: -7.37

 *** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one
*
 MeCN

E Param.: -6.75

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
5,7,7-trichloro-8(7H)-quinolinone
*
 MeCN

E Param.: -10.48

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
2,2,4-trichloro-1(2H)-naphthalenone
*
 MeCN

E Param.: -11.24

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
dibenzyl azodicarboxylate
*
 MeCN

E Param.: -8.89

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diethyl azodicarboxylate
*
 MeCN

E Param.: -10.15

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diisopropyl azodicarboxylate
*
 MeCN

E Param.: -10.71

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
di-tert-butyl azodicarboxylate
*
 MeCN

E Param.: -12.23

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
MacMillan-iminium ion (2nd generation)
*
 MeCN

E Param.: -5.52

 *** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
MacMillan-iminium ion (spiro)
*
 MeCN

E Param.: -7.67

 *** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
PhCH=N+Me2 (in MeCN)
C9H12N *
 MeCN

E Param.: -9.27

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
pTolCH=N+CH2 (in MeCN)
C10H14N *
 MeCN

E Param.: -9.64

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
p-AniCH=N+Me2 (in MeCN)
C10H14NO *
 MeCN

E Param.: -10.69

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)4 (in MeCN)
C11H14N *
 MeCN

E Param.: -9.35

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)5 (in MeCN)
C12H16N *
 MeCN

E Param.: -9.60

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
p-CF3-C6H4-CH=N+Me2 (in MeCN)
C10H11F3N *
 MeCN

E Param.: -8.34

 *** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ)
C8Cl2N2O2 *
 MeCN

E Param.: -3.66

 *** J. Am. Chem. Soc. 2013, 135, 12377-12387
10.1021/ja405890d
NFSI
C12H10FNO4S2 *
 MeCN

E Param.: -8.44

 *** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
phenyl isocyanate
C7H5NO *
 MeCN

E Param.: -15.38

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
p-tosyl isocyanate
C8H7NO3S *
 MeCN

E Param.: -7.69

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
1,2-diaza-1,3-diene 1e
*
 MeOH

E Param.: -14.90

 * Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1f
*
 MeOH

E Param.: -15.30

 * Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828