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)
fc(Ph)CH+
C17H15Fe *

E Param.: -2.64

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

E Param.: -8.54, Deviation: ±0.53

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
tropylium ion
C7H7 *

E Param.: -3.72, Deviation: ±0.03

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-phenyl-1,3-dithiolan-2-ylium ion
C9H9S2 *

E Param.: -5.91, Deviation: ±0.33

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-phenyl-1,3-dithianylium ion
C10H11S2 *

E Param.: -6.43, Deviation: ±0.04

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,3-dithianylium ion
C4H7S2 *

E Param.: -2.14, Deviation: ±0.07

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-ethylidenecarbazolium ion
C14H12N *

E Param.: 2.41, Deviation: ±0.33

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-methylacridinium ion
C14H12N *

E Param.: -7.15, Deviation: ±0.12

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
dimethylmethyleneammonium ion
C3H8N *

E Param.: -6.69

 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methyl(phenyl)methyleneammonium ion
C8H10N *

E Param.: -5.17

 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
Vilsmeier ion
C3H7ClN *

E Param.: -5.77

 * 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
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
flavylium ion
C15H11O *

E Param.: -3.45, Deviation: ±0.16

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(4-methoxyphenyl)chromenylium ion
C16H13O2 *

E Param.: -4.95, Deviation: ±0.06

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1,3-triphenylallylium ion
C21H17 *

E Param.: 0.98, Deviation: ±0.20

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1-dianisyl-3-phenylallylium ion
C23H21O2 *

E Param.: -2.67, Deviation: ±0.30

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion
*

E Param.: -8.97, Deviation: ±0.32

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion
C27H32N3 *

E Param.: -9.84, Deviation: ±0.21

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-phenylcyclopent-2-enylium ion
C11H11 *

E Param.: 2.89, Deviation: ±0.25

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(4-chlorophenyl)cyclopent-2-enylium ion
C11H10Cl *

E Param.: 3.20, Deviation: ±0.37

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
tritylium ion (Ph3C+)
C19H15 *

E Param.: 0.51

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
4,6-dinitrobenzofuroxan
C6H2N4O6 *

E Param.: -5.06

 *** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1,3,5-trinitrobenzene
C6H3N3O6 *

E Param.: -13.19, Deviation: ±0.45

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
6-nitro-tetrazolo[1,5a]pyridine
C5H3N5O2 *

E Param.: -9.05, Deviation: ±0.12

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan
C7H2F3N3O6S *

E Param.: -4.91, Deviation: ±0.31

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4,6-dinitrotetrazolopyridine
C5H2N6O4 *

E Param.: -4.67, Deviation: ±0.30

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4,6-dinitrobenzofurazan
C6H2N4O5 *

E Param.: -5.46, Deviation: ±0.36

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
2,4-dinitrothiophene
C4H2N2O4S *

E Param.: -12.33, Deviation: ±0.11

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
6-cyano-4-nitrobenzofuroxan
C7H2N4O4 *

E Param.: -7.01, Deviation: ±0.16

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4-cyano-6-nitro-benzofuroxane
C7H2N4O4 *

E Param.: -6.41, Deviation: ±0.38

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4-aza-6-nitrobenzofuroxan
C5H2N4O4 *

E Param.: -5.86, Deviation: ±0.36

 *** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
(2,4,6-trimethylphenyl)ethylium ion
C11H15 *

E Param.: 6.04

 * Macromolecules 2005, 38, 33-40
10.1021/ma048389o
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion
C22H29 *

E Param.: 6.16

 * Macromolecules 2005, 38, 33-40
10.1021/ma048389o
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione
C18H15NO2 *

E Param.: -13.56

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-(p-methoxybenzylidene)-indan-1,3-dione
C17H12O3 *

E Param.: -11.32

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-benzylidene-indan-1,3-dione
C16H10O2 *

E Param.: -10.11

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
jul-indan-1,3-dione
C22H19NO2 *

E Param.: -14.68

 *** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
aniBBS
C14H14N2O4 *

E Param.: -10.37

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dmaBBS
C15H17N3O3 *

E Param.: -12.76

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
julBBS
C19H21N3O3 *

E Param.: -13.84

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dma(S)BBS
C15H17N3O2S *

E Param.: -10.73

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
jul(S)BBS
C19H21N3O2S *

E Param.: -11.89

 *** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
4-nitrobenzodifuroxan (NBDF)
C6HN5O6 *

E Param.: -6.15

 *** Chem. Eur. J. 2007, 13, 8317-8324
10.1002/chem.200700676
benzylidene-Meldrum's acid
C13H12O4 *

E Param.: -9.15

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(methoxy)benzylidene Meldrum's acid
C14H14O5 *

E Param.: -10.28

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(dimethylamino)benzylidene Meldrum's acid
C15H17NO4 *

E Param.: -12.76

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
jul Meldrum's acid
C19H21NO4 *

E Param.: -13.97

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
diethyl benzylidene malonate
C14H16O4 *

E Param.: -20.55

 *** 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 4-cyano-benzylidene malonate
C15H15NO4 *

E Param.: -18.06

 *** 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-methyl-benzylidene malonate
C15H18O4 *

E Param.: -21.11

 *** 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-(dimethylamino)benzylidene malonate
C16H21NO4 *

E Param.: -23.10

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
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
Me2N+=CH-CH-Ph
C11H14N+ *

E Param.: -9.20

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
pyrN+=CH-CH-Ph
C13H16N+ *

E Param.: -9.80

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
pipN+=CH-CH-Ph
C14H18N+ *

E Param.: -10.30

 * Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(PhCH2)2N+=CH-CH-Ph
C23H22N+ *

E Param.: -8.50

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
Jorgensen/Hayashi-iminium ion
C29H34NOSi+ *

E Param.: -8.20

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
mor iminium
C13H16NO+ *

E Param.: -8.60

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone
C25H18O *

E Param.: -11.87

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
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-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
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
2,6-di-tert.butyl-4-(3-fluorobenzylidene)cyclohexa-2,5-dienone
C21H25FO *

E Param.: -15.03

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(3,5-difluorobenzylidene)cyclohexa-2,5-dienone
C21H24F2O *

E Param.: -14.50

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-dienone
C21H25NO3 *

E Param.: -14.36

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
(fur)(ani)CH+
C16H15O2 *

E Param.: -0.81

 ***** 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
(tfm)PhCH+
C14H10F3 *

E Param.: 6.70

 ***** 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
(mfp)2CH+
C13H9F2 *

E Param.: 6.87

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(dfp)(mfp)CH+
C13H8F3 *

E Param.: 7.52

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(tfm)2CH+
C15H9F6 *

E Param.: 7.96

 ** 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
(Ftol)2CH+
C15H13F2 *

E Param.: 5.24

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
p-quinone (C-H)
C6H4O2 *

E Param.: -16.19

 ** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
2,5-dichloroquinone (C-H)
C6H2Cl2O2 *

E Param.: -12.28

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
2,5-dichloroquinone (C-Cl)
C6H2Cl2O2 *

E Param.: -16.11

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-chloranil (C=O)
C6Cl4O2 *

E Param.: -12.13

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-chloranil (C-Cl)
C6Cl4O2 *

E Param.: -13.84

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-fluoranil (C=O)
C6F4O2 *

E Param.: -9.37

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-fluoranil (C-F)
C6F4O2 *

E Param.: -11.12

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
o-chloranil (C=O)
C6Cl4O2 *

E Param.: -8.77

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
o-chloranil (C-Cl)
C6Cl4O2 *

E Param.: -12.02

 *** J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
3-benzylidene-1-methyl-3H-indol-1-ium ion
C16H14N *

E Param.: -1.80

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
1-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion
C17H16N *

E Param.: -2.19

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
3-(4-methoxybenzylidene)-1-methyl-3H-indol-1-ium iom
C17H16NO *

E Param.: -3.02

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
3-(4-(dimethylamino)benzylidene)-1-methyl-3H-indol-1-ium ion
C18H19N2 *

E Param.: -6.26

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
1-methyl-3-((julolidin-9-yl)methylene)-3H-indol-1-ium ion
C22H23N2 *

E Param.: -7.79

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
(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)-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)-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
bis(1-methylindol-3-yl)methylium ion
C19H17N2 *

E Param.: -5.99

 *** J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298