Mayr's Database of Reactivity Parameters

Carbocations

For reactivities of structurally related compounds go to: Electrophiles » C-Electrophiles » Carbocations

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
(PhCH2)2N+=CH-CH-Ph
C23H22N+ *

E Param.: -8.50

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(pyr)2CH+
C21H25N2 *

E Param.: -7.69

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(S,E)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)-5-(3,4,5-trimethoxybenzyl)imidazolidin-1-ium
C25H31N2O4 *
 dichloromethane

E Param.: -7.00

 ** Angew. Chem. Int. Ed. 2013, 52, 7967-7971
10.1002/anie.201301864
(S,E)-2,2,3-trimethyl-4-oxo-5-((perfluorophenyl)methyl)-1-((E)-3-phenylallylidene)imidazolidin-1-ium
C22H20F5N2O *
 dichloromethane

E Param.: -6.00

 ** Angew. Chem. Int. Ed. 2013, 52, 7967-7971
10.1002/anie.201301864
(S,E)-5-((1H-indol-3-yl)methyl)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)imidazolidin-1-ium
C24H26N3O *
 dichloromethane

E Param.: -7.30

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C24H30N3O *
 dichloromethane

E Param.: -10.60

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-cyanophenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C23H24N3O *
 dichloromethane

E Param.: -6.00

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-1-((E)-3-(4-methoxyphenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C23H27N2O2 *
 dichloromethane

E Param.: -8.00

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(3-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium
C22H24N3O3 *
 dichloromethane

E Param.: -6.10

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-1-((E)-3-(4-nitrophenyl)allylidene)-4-oxoimidazolidin-1-ium
C22H24N3O3 *
 dichloromethane

E Param.: -5.90

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-4-oxo-1-((E)-3-(p-tolyl)allylidene)imidazolidin-1-ium
C23H27N2O *
 dichloromethane

E Param.: -7.20

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(tfm)2CH+
C15H9F6 *

E Param.: 7.96

 ** 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
(thq)2CH+
C21H25N2 *

E Param.: -8.22

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(tol)2CH+
C15H15 *

E Param.: 3.63

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1,1,3-triphenylallylium ion
C21H17 *

E Param.: 0.98, Deviation: ±0.20

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

E Param.: -9.84, Deviation: ±0.21

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

E Param.: -2.67, Deviation: ±0.30

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion
C22H29 *

E Param.: 6.16

 * Macromolecules 2005, 38, 33-40
10.1021/ma048389o
1,3-dithianylium ion
C4H7S2 *

E Param.: -2.14, Deviation: ±0.07

 *** 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
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
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
1-phenylcyclopent-2-enylium ion
C11H11 *

E Param.: 2.89, Deviation: ±0.25

 *** 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
2-phenyl-1,3-dithianylium ion
C10H11S2 *

E Param.: -6.43, Deviation: ±0.04

 *** 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
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
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-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
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium
C21H30N *
 dichloromethane

E Param.: -4.51

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
9-(4-methoxyphenyl)-9H-fluoren-9-ylium
C20H27O *
 dichloromethane

E Param.: 0.85

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
9-phenyl-9H-fluoren-9-ylium
C19H25 *
 dichloromethane

E Param.: 2.41

 *** Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
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(tol)CH+
C15H15O *

E Param.: 1.48

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
benzhydrylium ion Ph2CH+
C13H11 *

E Param.: 5.47

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
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
cumyl cation
*

E Param.: 5.74

 *** Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
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
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