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)
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
((2-(2-iodophenyl)propan-2-yl)oxy)(trifluoromethyl)sulfane
*

E Param.: -14.52

 *** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
((2-phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane
*

E Param.: -13.77

 *** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
(2,4,6-trimethylphenyl)ethylium ion
C11H15 *

E Param.: 6.04

 * Macromolecules 2005, 38, 33-40
10.1021/ma048389o
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene
*
 DMSO

E Param.: -13.88

 *** 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
(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
(3-CF3)-tritylium ion
*

E Param.: 1.18

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)-tritylium ion
*

E Param.: 1.06

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)3-tritylium ion
*

E Param.: 1.99

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-F)-tritylium ion
*

E Param.: 1.01

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)2-tritylium ion
*

E Param.: 1.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)3-tritylium ion
*

E Param.: 2.07

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)4-tritylium ion
*

E Param.: 2.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-CF3)-tritylium ion
*

E Param.: 1.33

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-CF3)2-tritylium ion
*

E Param.: 2.28

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-F)-tritylium ion
*

E Param.: 0.35

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)2-tritylium ion
*

E Param.: 0.17

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)3-tritylium ion
*

E Param.: 0.05

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-Me)-tritylium ion
*

E Param.: -0.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)2-tritylium ion
*

E Param.: -0.70

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)3-tritylium ion
*

E Param.: -1.21

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)-tritylium ion
*

E Param.: -1.59

 - Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-MeO)2-tritylium ion
*

E Param.: -3.04

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)3-tritylium ion
*

E Param.: -4.35

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO,3-OMe)-tritylium ion
*

E Param.: -1.62

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO,4-Me)-tritylium ion
*

E Param.: -2.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)-tritylium ion
*

E Param.: -7.93

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-OMe,3-Me)-tritylium ion
*

E Param.: -1.84

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(ani)2CH+
C15H15O2 *

E Param.: 0.00

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(dfp)(mfp)CH+
C13H8F3 *

E Param.: 7.52

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(dfp)2CH+
C13H7F4 *

E Param.: 8.02

 * J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(dfp)PhCH+
C13H9F2 *

E Param.: 6.74

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(dma)2CH+
C17H21N2 *

E Param.: -7.02

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(dpa)2CH+
C37H29N2 *

E Param.: -4.72

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(E)-1,2-dimethyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion
C18H18N *

E Param.: -5.05

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
(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)-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
(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)-2,6-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.[...]
(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-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-(4-methoxybenzylidene)acenaphthylen-1(2H)-one
C20H14O2 *

E Param.: -18.72

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061
(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
(E)-2-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion
C17H16N *

E Param.: -5.15

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
(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)-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-benzylidene-1,2-dimethyl-3H-indol-1-ium ion
C17H16N *

E Param.: -4.96

 ** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
(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
(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-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
(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-((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-((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
(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-(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-(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-(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-(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-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-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-(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-benzylidenebenzo[d][1,3]dioxol-5(6H)-one
C14H10O3 *

E Param.: -14.47

 *** Chem. Eur. J. 2025, 31, e202403785
10.1002/chem.202403785
(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)-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-benzylidene-4-methylbenzenesulfonamide (in DMSO)
C14H13NO2S *
 DMSO

E Param.: -11.50

 *** 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
(E)-tert-butyl benzylidenecarbamate (in DMSO)
C12H15NO2 *
 DMSO

E Param.: -14.22

 *** 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
(Ftol)2CH+
C15H13F2 *

E Param.: 5.24

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(fur)(ani)CH+
C16H15O2 *

E Param.: -0.81

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(fur)2CH+
C17H15O2 *

E Param.: -1.36

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(ind)2CH+
C19H21N2 *

E Param.: -8.76

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(jul)2CH+
C25H29N2 *

E Param.: -9.45

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(lil)2CH+
C23H25N2 *

E Param.: -10.04

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mfa)2CH+
C19H19F6N2 *

E Param.: -3.85

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mfp)2CH+
C13H9F2 *

E Param.: 6.87

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(mfp)PhCH+
C13H10F *

E Param.: 6.23

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(mor)2CH+
C21H25N2O2 *

E Param.: -5.53

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mpa)2CH+
C27H25N2 *

E Param.: -5.89

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(p-nitrophenyl)diazomethane
C7H5N3O2 *

E Param.: -18.30

 *** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
(pcp)2CH+
C13H9Cl2 *

E Param.: 5.48

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(pfa)2CH+
C29H23F6N2 *

E Param.: -3.14

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(pfp)2CH+
C13H9F2 *

E Param.: 5.01, Deviation: ±0.05

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(PhCH2)2N+=CH-CH-Ph
C23H22N+ *

E Param.: -8.50

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(pyr)2CH+
C21H25N2 *

E Param.: -7.69

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(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)-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)-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
(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-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-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-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-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
(tfm)2CH+
C15H9F6 *

E Param.: 7.96

 ** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(tfm)PhCH+
C14H10F3 *

E Param.: 6.70

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b