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)
9-phenyl-9H-fluoren-9-ylium
C19H25 *
 dichloromethane

E Param.: 2.41

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
<i>trans-beta</i>-nitrostyrene
*

E Param.: -13.85

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
acrylonitrile (in DMSO)
C3H3N *
 DMSO

E Param.: -19.05

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
ani(Br)2QM
C14H10Br2O2 *

E Param.: -8.63

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
ani(Ph)2QM
C26H20O2 *

E Param.: -12.18

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
ani(Ph)CH+
C14H13O *

E Param.: 2.11

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
ani(pop)CH+
C20H17O2 *

E Param.: 0.61

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
ani(t-Bu)2QM
*

E Param.: -16.11

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
ani(tol)CH+
C15H15O *

E Param.: 1.48

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
aniBBS
C14H14N2O4 *

E Param.: -10.37

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
benzaldehyde (in DMSO)
C7H6O *
 DMSO

E Param.: -12.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
benzaldehyde-boron trichloride complex
*

E Param.: 1.12, Deviation: ±0.24

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
benzhydrylium ion Ph2CH+
C13H11 *

E Param.: 5.47

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
benzylidene-Meldrum's acid
C13H12O4 *

E Param.: -9.15

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
benzylidenemalononitrile
C10H6N2 *

E Param.: -9.42

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
bh 6f
*

E Param.: -18.90

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

E Param.: -19.10

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

E Param.: -18.20

 * 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
bh 6m
*

E Param.: -17.30

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh6a
*

E Param.: -18.60

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh6j
*

E Param.: -17.90

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
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
bis(1-methylindol-3-yl)methylium ion
C19H17N2 *

E Param.: -5.99

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
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(julidin-9-yl)allylium ion
*

E Param.: -9.78

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
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
butanal (in DMSO)
C4H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
butynone
C4H4O *

E Param.: -16.60

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
C6H6OMe+-Fe(CO)3
*

E Param.: -8.94, Deviation: ±0.13

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C6H7+-Fe(CO)3
*

E Param.: -7.76, Deviation: ±0.31

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C7H7+-Fe(CO)3
*

E Param.: -3.49, Deviation: ±0.17

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C7H9+-Fe(CO)3
*

E Param.: -9.21, Deviation: ±0.36

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
carbon disulfide
CS2 *
 DMSO

E Param.: -17.70

 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
cinnamaldehyde (in DMSO)
C9H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
cinnamonitrile (in DMSO)
C9H7N *
 DMSO

E Param.: -24.60

 * J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
cumyl cation
*

E Param.: 5.74

 *** Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
cyclobutanone (in DMSO)
C4H6O *
 DMSO

E Param.: -17.50

 * 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
cycloheptenone
C7H10O *
 DMSO

E Param.: -22.00

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclohexanone (in DMSO)
C6H10O *
 DMSO

E Param.: -19.90

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

E Param.: -22.10

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
cyclopentanone (in DMSO)
C5H8O *
 DMSO

E Param.: -21.00

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
cyclopentenone
C5H6O *
 DMSO

E Param.: -20.60

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
di-p-anisyl-allylium ion
*

E Param.: -1.45

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
di-p-tolyl-allylium ion
*

E Param.: 1.23

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
di-tert-butyl azodicarboxylate
*
 MeCN

E Param.: -12.23

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diarylallylium ion (3,3-F2)2
*

E Param.: 6.11

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (3-F)2
*

E Param.: 4.15

 ** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-Br)2
*

E Param.: 2.85

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-Cl)2
*

E Param.: 2.69

 * J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-NMe2)2
*

E Param.: -7.50

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
dibenzo[a,d]tropylium ion
C15H11 *
 dichloromethane

E Param.: -0.63

 - Liebigs Ann. 1995, , 2005-2009
10.1002/jlac.1995199[...]
dibenzyl azodicarboxylate
*
 MeCN

E Param.: -8.89

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
dicarbonyl(cyclopentadienyl)propene-iron(II)
*

E Param.: -11.20

 *** Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
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
diethyl 2-((julolidine-9-yl)methylene)malonate
C20H25NO4 *

E Param.: -23.80

 * Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 3-chloro-benzylidene malonate
C14H15ClO4 *

E Param.: -18.98

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-(dimethylamino)benzylidene malonate
C16H21NO4 *

E Param.: -23.10

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-cyano-benzylidene malonate
C15H15NO4 *

E Param.: -18.06

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-methoxy-benzylidene malonate
C15H18O5 *

E Param.: -21.47

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-methyl-benzylidene malonate
C15H18O4 *

E Param.: -21.11

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-nitrobenzylidene malonate
C14H15NO6 *

E Param.: -17.67

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl azodicarboxylate
*
 MeCN

E Param.: -10.15

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diethyl benzylidene malonate
C14H16O4 *

E Param.: -20.55

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
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
dihydro-2H-pyran-2-one
C5H6O2 *
 DMSO

E Param.: -21.80

 ** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
diisopropyl azodicarboxylate
*
 MeCN

E Param.: -10.71

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
dimethyl diazomalonate
C5H6N2O4 *

E Param.: -18.20

 *** Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
dimethylmethyleneammonium ion
C3H8N *

E Param.: -6.69

 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
diphenylallylium ion
*

E Param.: 2.70

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diphenylcarbodiimide
C13H10N2 *
 DMSO

E Param.: -20.14

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

E Param.: -21.40

 - Chem. Eur. J. 2022, 28, e202201376
10.1002/chem.202201376
dma(Ph)2QM
C27H23NO *

E Param.: -13.39

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
dma(S)BBS
C15H17N3O2S *

E Param.: -10.73

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dma(t-Bu)2QM
*

E Param.: -17.29

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
dmaBBS
C15H17N3O3 *

E Param.: -12.76

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
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.[...]
ethenesulfonyl fluoride (ESF)
*
 DMSO

E Param.: -12.09

 *** Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
ethenylsulfonylbenzene (in DMSO)
C8H8O2S *
 DMSO

E Param.: -18.36

 *** 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 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
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 3-nitro-1H-indole-1-carboxylate
C11H10N2O4 *

E Param.: -14.10

 ** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
ethyl cinnamate (in DMSO)
C11H12O2 *
 DMSO

E Param.: -24.52

 ** 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
fc(ani)CH+
C18H17FeO *

E Param.: -2.90, Deviation: ±0.09

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
fc(Me)CH+
C12H13Fe *

E Param.: -2.57

 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
fc(Ph)CH+
C17H15Fe *

E Param.: -2.64

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
fc2CH+
C21H19Fe2 *

E Param.: -8.54, Deviation: ±0.53

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
flavylium ion
C15H11O *

E Param.: -3.45, Deviation: ±0.16

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
fumaronitrile
C4H2N2 *
 DMSO

E Param.: -15.71

 *** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
furan-2(5H)-one
C4H4O2 *
 DMSO

E Param.: -20.70

 *** Chem. Sci. 2021, 12, 4850-4865
10.1039/D0SC06628A
hex-3-yn-2-one
C6H8O *

E Param.: -17.90

 - Angew. Chem. Int. Ed. 2019, 58, 17704-17708
10.1002/anie.201909803
hexanal (in DMSO)
C6H12O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
indolecarboxylate derived iminium ion
*
 dichloromethane

E Param.: -9.50

 ** Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
Jorgensen/Hayashi-iminium ion
C29H34NOSi+ *

E Param.: -8.20

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
jul Meldrum's acid
C19H21NO4 *

E Param.: -13.97

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
jul(S)BBS
C19H21N3O2S *

E Param.: -11.89

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g