Mayr's Database of Reactivity Parameters

C-Electrophiles

For reactivities of structurally related compounds go to: Electrophiles » C-Electrophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
bis(5-methoxy-1-methylindol-3-yl)methylium ion
C21H21N2O2 *

E Param.: -6.90

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
bis(1,2-dimethylindol-3-yl)methylium ion
C21H21N2 *

E Param.: -10.23

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
ethyl 3-nitro-1H-indole-1-carboxylate
C11H10N2O4 *

E Param.: -14.10

 ** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
3-nitro-1-tosyl-1H-indole
C15H12N2O4S *

E Param.: -14.87

 *** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
4-bromo-3-nitro-1-tosyl-1H-indole
C15H11BrN2O4S *

E Param.: -14.60

 ** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
3,6-dinitro-1-tosyl-1H-indole
*

E Param.: -12.90

 *** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
4-phenylbut-3-yn-2-one
C10H8O *

E Param.: -16.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
hex-3-yn-2-one
C6H8O *

E Param.: -17.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
butynone
C4H4O *

E Param.: -16.60

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
Umemoto I (triflate)
*

E Param.: -13.08

 *** Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
Umemoto I (tetrafluoroborate)
*

E Param.: -13.39

 *** Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
Umemoto II (triflate)
*

E Param.: -12.80

 *** Eur. J. Org. Chem. 2024, 27, e202400085
10.1002/ejoc.202400085
(E)-6-(4-nitrobenzylidene)benzo[d][1,3]dioxol-5(6H)-one
C14H9NO5 *

E Param.: -13.15

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(4-(trifluoromethyl)benzylidene)benzo[d][1,3]dioxol-5(6H)-one
C15H9F3O3 *

E Param.: -13.54

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(3-fluorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one
C14H9FO3 *

E Param.: -14.00

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(4-chlorobenzylidene)benzo[d][1,3]dioxol-5(6H)-one
C14H9ClO3 *

E Param.: -13.99

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-benzylidenebenzo[d][1,3]dioxol-5(6H)-one
C14H10O3 *

E Param.: -14.47

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(4-methylbenzylidene)benzo[d][1,3]dioxol-5(6H)-one
C15H12O3 *

E Param.: -14.85

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(4-methoxybenzylidene)benzo[d][1,3]dioxol-5(6H)-one
C15H12O4 *

E Param.: -15.20

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(4-(dimethylamino)benzylidene)benzo[d][1,3]dioxol-5(6H)-one
C16H15NO3 *

E Param.: -16.07

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(E)-6-(furan-2-ylmethylene)benzo[d][1,3]dioxol-5(6H)-one
C12H8O4 *

E Param.: -15.73

 *** Org. Biomol. Chem. 2025, 23, 827-834
10.1039/D4OB01855A
(E)-6-((1-methyl-1H-pyrrol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one
C13H11NO3 *

E Param.: -17.03

 *** Org. Biomol. Chem. 2025, 23, 827-834
10.1039/D4OB01855A
(E)-6-((1-methyl-1H-indol-2-yl)methylene)benzo[d][1,3]dioxol-5(6H)-one
C17H13NO3 *

E Param.: -15.55

 *** Org. Biomol. Chem. 2025, 23, 827-834
10.1039/D4OB01855A
(E)-6-((E)-3-phenylallylidene)benzo[d][1,3]dioxol-5(6H)-one
C16H12O3 *

E Param.: -16.00

 *** Org. Biomol. Chem. 2025, 23, 827-834
10.1039/D4OB01855A
2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dien-1-one
C15H22O *

E Param.: -11.17

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
2,6-di-tert-butyl-4-(methoxymethylene)cyclohexa-2,5-dien-1-one
C16H24O2 *

E Param.: -15.10

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetonitrile
C16H21NO *

E Param.: -11.88

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
ethyl 2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetate
C18H26O3 *

E Param.: -12.01

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-dien-1-one
C16H24O *

E Param.: -13.68

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
4-benzylidene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one
C21H26O *

E Param.: -15.58

 *** Chem. Eur. J. 2025, 31, e202501224
10.1002/chem.202501224
Me2C=C=N(+)Me2
*

E Param.: -2.80

 - Synthesis 2025, 57, 3251-3262
10.1055/a-2649-1999
Ph2C=C=N(+)Me2
*

E Param.: -1.90

 - Synthesis 2025, 57, 3251-3262
10.1055/a-2649-1999
(E)-10-(4-methoxybenzylidene)phenanthren-9(10H)-one
C22H16O2 *

E Param.: -15.93

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061
(E)-2-(4-methoxybenzylidene)acenaphthylen-1(2H)-one
C20H14O2 *

E Param.: -18.72

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061
indolecarboxylate derived iminium ion
*
 dichloromethane

E Param.: -9.50

 ** Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(S,E)-2,2,3-trimethyl-4-oxo-5-((perfluorophenyl)methyl)-1-((E)-3-phenylallylidene)imidazolidin-1-ium
C22H20F5N2O *
 dichloromethane

E Param.: -6.00

 ** Angew. Chem. Int. Ed. 2013, 52, 7967-7971
10.1002/anie.201301864
(S,E)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)-5-(3,4,5-trimethoxybenzyl)imidazolidin-1-ium
C25H31N2O4 *
 dichloromethane

E Param.: -7.00

 ** Angew. Chem. Int. Ed. 2013, 52, 7967-7971
10.1002/anie.201301864
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(4-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium
C22H24N3O3 *
 dichloromethane

E Param.: -5.90

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-cyanophenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C23H24N3O *
 dichloromethane

E Param.: -6.00

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C24H30N3O *
 dichloromethane

E Param.: -10.60

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-4-oxo-1-((E)-3-(p-tolyl)allylidene)imidazolidin-1-ium
C23H27N2O *
 dichloromethane

E Param.: -7.20

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-methoxyphenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C23H27N2O2 *
 dichloromethane

E Param.: -8.00

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(3-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium
C22H24N3O3 *
 dichloromethane

E Param.: -6.10

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-((1H-indol-3-yl)methyl)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)imidazolidin-1-ium
C24H26N3O *
 dichloromethane

E Param.: -7.30

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(2S,5S)-5-benzyl-3-methyl-4-oxo-1-(3-phenylallylidene)-2-((E)-styryl)imidazolidin-1-ium
C28H27N2O *
 dichloromethane

E Param.: -5.90

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
dibenzo[a,d]tropylium ion
C15H11 *
 dichloromethane

E Param.: -0.63

 - Liebigs Ann. 1995, , 2005-2009
10.1002/jlac.1995199[...]
(E)-2-(tert-butyl)-3-(4-methylbenzylidene)-3H-indol-1-ium
C20H22N+ *
 dichloromethane

E Param.: -5.06

 * Eur. J. Org. Chem. 2016, , 4050-4058
10.1002/ejoc.201600572
9-phenyl-9H-fluoren-9-ylium
C19H25 *
 dichloromethane

E Param.: 2.41

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
9-(4-methoxyphenyl)-9H-fluoren-9-ylium
C20H27O *
 dichloromethane

E Param.: 0.85

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium
C21H30N *
 dichloromethane

E Param.: -4.51

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
1,2-diaza-1,3-diene 1a
*
 DMSO

E Param.: -13.28

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

E Param.: -13.90

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

E Param.: -14.91

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

E Param.: -15.38

 *** Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
(E)-3-(4-nitro-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.33

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-3-(4-cyano-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.64

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-1,3-diphenylprop-2-en-1-one (in DMSO)
C15H12O *
 DMSO

E Param.: -19.39

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-4-(4-nitrophenyl)but-3-en-2-one (in DSMO)
C10H9NO3 *
 DMSO

E Param.: -19.36

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4-methyl-1-(4-nitrophenyl)pent-1-en-3-one (in DMSO)
C12H13NO3 *
 DMSO

E Param.: -19.17

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4,4-dimethyl-1-(4-nitrophenyl)pent-1-en-3-one
C13H15NO3 *
 DMSO

E Param.: -19.15

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-chloro-benzaldehyde (in DMSO)
C7H5ClO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-fluoro-benzaldehyde (in DMSO)
C7H5FO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-methoxy-benzaldehyde (in DMSO)
C8H8O2 *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
4-fluoro-benzaldehyde (in DMSO)
C7H5FO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
benzaldehyde (in DMSO)
C7H6O *
 DMSO

E Param.: -12.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
hexanal (in DMSO)
C6H12O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
butanal (in DMSO)
C4H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
cinnamaldehyde (in DMSO)
C9H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
p-nitro-cinnamaldehyde (in DMSO)
C9H7NO3 *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)
C14H13NO2S *
 DMSO

E Param.: -11.50

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO)
C15H15NO3S *
 DMSO

E Param.: -13.05

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-(4-(dimethylamino)benzylidene)-4-methylbenzenesulfonamide (in DMSO)
C16H18N2O2S *
 DMSO

E Param.: -15.09

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-tert-butyl benzylidenecarbamate (in DMSO)
C12H15NO2 *
 DMSO

E Param.: -14.22

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-benzylidene-P,P-diphenylphosphinic amide
C19H16NOP *
 DMSO

E Param.: -15.89

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(ethene-1,1-diyldisulfonyl)dibenzene
*
 DMSO

E Param.: -7.50

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
(2-phenylethene-1,1-diyldisulfonyl)dibenzene
*
 DMSO

E Param.: -12.93

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene
*
 DMSO

E Param.: -13.88

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
4-(2,2-bis(phenylsulfonyl)vinyl)-N,N-dimethylaniline
*
 DMSO

E Param.: -16.53

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
 DMSO

E Param.: -11.78

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2-(4-methoxybenzylidene)benzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
 DMSO

E Param.: -13.02

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2-(4-methoxybenzylidene)-1,3-dithiane 1,1,3,3-tetraoxide
*
 DMSO

E Param.: -14.55

 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium
C14H15N2O *
 DMSO

E Param.: -11.52

 *** Angew. Chem. Int. Ed. 2012, 51, 5234-5238
10.1002/anie.201109042
maleic anhydride
C4H4O3 *
 DMSO

E Param.: -11.31

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