Mayr's Database of Reactivity Parameters

C-Electrophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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 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
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
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
jul(t-Bu)2QM
*

E Param.: -17.90

**** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
jul-indan-1,3-dione
C22H19NO2 *

E Param.: -14.68

*** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
julBBS
C19H21N3O3 *

E Param.: -13.84

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
MacMillan-iminium ion (1st generation)
C22H25N2O+ *
MeCN

E Param.: -7.37

*** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
MacMillan-iminium ion (2nd generation)
*
MeCN

E Param.: -5.52

*** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
MacMillan-iminium ion (spiro)
*
MeCN

E Param.: -7.67

*** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
maleic anhydride
C4H4O3 *
DMSO

E Param.: -11.31

*** Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
Me2C=C=N(+)Me2
*

E Param.: -2.80

- Synthesis 2025, 57, 3251-3262
10.1055/a-2649-1999
Me2N+=CH-CH-Ph
C11H14N+ *

E Param.: -9.20

*** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
methoxy-(4-methoxyphenyl)methylium ion
C9H11O2 *

E Param.: 0.14, Deviation: ±0.01

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methoxy-(4-methylphenyl)methylium ion
C9H11O *

E Param.: 1.90, Deviation: ±0.22

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methoxy-phenylmethylium ion
C8H9O *

E Param.: 2.97, Deviation: ±0.09

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