Mayr's Database of Reactivity Parameters

Electrophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
N-(phenylsulfonyl)-N-((trifluoromethyl)thio)benzenesulfonamide
*

E Param.: -6.06

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate
*

E Param.: -10.46

*** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
N-fluoro-2,6-dichloropyridinium tetrafluoroborate
*

E Param.: -5.29

*** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
Selectfluor
C7H14ClFN2 *

E Param.: -5.20

*** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
NFSI
C12H10FNO4S2 *
MeCN

E Param.: -8.44

*** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
N-fluoropyridinium tetrafluoroborate
C5H5FN *

E Param.: -9.89

*** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
N-(trifluoromethyl)thio)phthalimide
*

E Param.: -11.92

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-(trifluoromethyl)thio)saccharin
*

E Param.: -6.48

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-(trifluoromethyl)thio)succinimide
*

E Param.: -12.56

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-(difluoromethyl)thio)phthalimide
*

E Param.: -11.86

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-methyl-N-((trifluoromethyl)thio)-p-toluenesulfonamide
*

E Param.: -13.44

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
N-methyl-N-((trifluoromethyl)thio)-aniline
*

E Param.: -23.32

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

E Param.: -14.52

*** Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
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
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
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
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
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
cycloheptenone
C7H10O *
DMSO

E Param.: -22.00

*** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
methyl diazoacetate
C3H4N2O2 *

E Param.: -18.50

*** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
dimethyl diazomalonate
C5H6N2O4 *

E Param.: -18.20

*** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
(p-nitrophenyl)diazomethane
C7H5N3O2 *

E Param.: -18.30

*** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
diphenyldiazomethane
C13H10N2 *

E Param.: -21.40

- Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
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