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)
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
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
3-methylcyclohexenone
C7H10O *
 DMSO

E Param.: -29.60

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

E Param.: -28.90

 * 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
(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
cinnamonitrile (in DMSO)
C9H7N *
 DMSO

E Param.: -24.60

 * 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
diethyl 2-((julolidine-9-yl)methylene)malonate
C20H25NO4 *

E Param.: -23.80

 * Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
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
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
diethyl 2-((1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)methylene)malonate
C18H23NO4 *

E Param.: -23.40

 * Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
N-methyl-N-((trifluoromethyl)thio)-aniline
*

E Param.: -23.32

 * Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
diethyl 4-(dimethylamino)benzylidene malonate
C16H21NO4 *

E Param.: -23.10

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
(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
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
pentan-2-one (in DMSO)
C5H10O *
 DMSO

E Param.: -22.30

 * 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
2-methylcyclopentenone
C6H8O *
 DMSO

E Param.: -22.10

 *** 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
cycloheptenone
C7H10O *
 DMSO

E Param.: -22.00

 *** 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
diethyl 4-methoxy-benzylidene malonate
C15H18O5 *

E Param.: -21.47

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diphenyldiazomethane
C13H10N2 *

E Param.: -21.40

 - Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
diethyl 4-methyl-benzylidene malonate
C15H18O4 *

E Param.: -21.11

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
cyclopentanone (in DMSO)
C5H8O *
 DMSO

E Param.: -21.00

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
furan-2(5H)-one
C4H4O2 *
 DMSO

E Param.: -20.70

 *** 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
diethyl benzylidene malonate
C14H16O4 *

E Param.: -20.55

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
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
diphenylcarbodiimide
C13H10N2 *
 DMSO

E Param.: -20.14

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
cyclohexanone (in DMSO)
C6H10O *
 DMSO

E Param.: -19.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
3-methylenetetrahydropyran-2-one
C6H8O2 *
 DMSO

E Param.: -19.50

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
diethyl maleate
C8H12O4 *
 DMSO

E Param.: -19.49

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
3-methylenedihydrofuranone
C5H6O2 *
 DMSO

E Param.: -19.40

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
(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
bh 6i
*

E Param.: -19.10

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
ethyl prop-2-enoate (in DMSO)
C5H8O2 *
 DMSO

E Param.: -19.07

 *** 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
diethyl 3-chloro-benzylidene malonate
C14H15ClO4 *

E Param.: -18.98

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
bh 6f
*

E Param.: -18.90

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6l
*

E Param.: -18.90

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
methyl prop-2-enoate (in DMSO)
C4H6O2 *
 DMSO

E Param.: -18.84

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-2-(4-methoxybenzylidene)acenaphthylen-1(2H)-one
C20H14O2 *

E Param.: -18.72

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061
bh6a
*

E Param.: -18.60

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
methyl diazoacetate
C3H4N2O2 *

E Param.: -18.50

 *** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
1-methylpiperidin-4-one (in DMSO)
C6H11NO *
 DMSO

E Param.: -18.40

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
ethenylsulfonylbenzene (in DMSO)
C8H8O2S *
 DMSO

E Param.: -18.36

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(p-nitrophenyl)diazomethane
C7H5N3O2 *

E Param.: -18.30

 *** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
bh 6k
*

E Param.: -18.20

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
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
dimethyl diazomalonate
C5H6N2O4 *

E Param.: -18.20

 *** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
phenyl isothiocyanate
C7H5NS *
 DMSO

E Param.: -18.15

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
diethyl 4-cyano-benzylidene malonate
C15H15NO4 *

E Param.: -18.06

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
jul(t-Bu)2QM
*

E Param.: -17.90

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
bh6j
*

E Param.: -17.90

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
oxan-4-one (in DMSO)
C5H8O2 *
 DMSO

E Param.: -17.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
hex-3-yn-2-one
C6H8O *

E Param.: -17.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
diethyl fumarate
C8H12O4 *
 DMSO

E Param.: -17.79

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
carbon disulfide
CS2 *
 DMSO

E Param.: -17.70

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
diethyl 4-nitrobenzylidene malonate
C14H15NO6 *

E Param.: -17.67

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
(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
cyclobutanone (in DMSO)
C4H6O *
 DMSO

E Param.: -17.50

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
(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)-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
bh 6m
*

E Param.: -17.30

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
dma(t-Bu)2QM
*

E Param.: -17.29

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
2,6-dimethoxy-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone
C17H19NO3 *

E Param.: -17.18

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
(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)-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.[...]
thian-4-one (in DMSO)
C5H8OS *
 DMSO

E Param.: -16.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
4-phenylbut-3-yn-2-one
C10H8O *

E Param.: -16.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
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.[...]
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
2-phenylethene-1-sulfonyl fluoride
C8H7FO2S *
 DMSO

E Param.: -16.63

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
butynone
C4H4O *

E Param.: -16.60

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
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
2,6-dimethoxy-4-(4-methoxybenzylidene)cyclohexa-2,5-dienone
C16H16O4 *

E Param.: -16.38

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-dimethyl-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone
C17H19NO *

E Param.: -16.36

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
(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.[...]
p-quinone (C-H)
C6H4O2 *

E Param.: -16.19

 ** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
ani(t-Bu)2QM
*

E Param.: -16.11

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
2,5-dichloroquinone (C-Cl)
C6H2Cl2O2 *

E Param.: -16.11

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
(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-((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)-10-(4-methoxybenzylidene)phenanthren-9(10H)-one
C22H16O2 *

E Param.: -15.93

 *** J. Phys. Org. Chem. 2026, 39, e70061
10.1002/poc.70061
(E)-N-benzylidene-P,P-diphenylphosphinic amide
C19H16NOP *
 DMSO

E Param.: -15.89

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
p-nitrophenyl isothiocyanate
C7H4N2O2S *
 DMSO

E Param.: -15.89

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
tol(t-Bu)2QM
C22H28O *

E Param.: -15.83

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
(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
fumaronitrile
C4H2N2 *
 DMSO

E Param.: -15.71

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