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)
tritylium ion (Ph3C+)
C19H15 *

E Param.: 0.51

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-CF3)2-tritylium ion
*

E Param.: 2.28

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)3-tritylium ion
*

E Param.: 1.99

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-CF3)-tritylium ion
*

E Param.: 1.33

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)-tritylium ion
*

E Param.: 1.06

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-CF3)-tritylium ion
*

E Param.: 1.18

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)-tritylium ion
*

E Param.: -0.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)2-tritylium ion
*

E Param.: -0.70

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)3-tritylium ion
*

E Param.: -1.21

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO,3-OMe)-tritylium ion
*

E Param.: -1.62

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-OMe,3-Me)-tritylium ion
*

E Param.: -1.84

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)-tritylium ion
*

E Param.: -1.59

 - Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-MeO,4-Me)-tritylium ion
*

E Param.: -2.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)2-tritylium ion
*

E Param.: -3.04

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)3-tritylium ion
*

E Param.: -4.35

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)-tritylium ion
*

E Param.: -7.93

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
dibenzo[a,d]tropylium ion
C15H11 *
 dichloromethane

E Param.: -0.63

 - Liebigs Ann. 1995, , 2005-2009
10.1002/jlac.1995199[...]
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
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
(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
pipN+=CH-CH-Ph
C14H18N+ *

E Param.: -10.30

 * Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(4-F)-tritylium ion
*

E Param.: 0.35

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)2-tritylium ion
*

E Param.: 0.17

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)3-tritylium ion
*

E Param.: 0.05

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)-tritylium ion
*

E Param.: 1.01

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)2-tritylium ion
*

E Param.: 1.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)3-tritylium ion
*

E Param.: 2.07

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)4-tritylium ion
*

E Param.: 2.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
diarylallylium ion (4-Cl)2
*

E Param.: 2.69

 * J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
(dfp)2CH+
C13H7F4 *

E Param.: 8.02

 * J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(E)-2-(tert-butyl)-3-(4-methylbenzylidene)-3H-indol-1-ium
C20H22N+ *
 dichloromethane

E Param.: -5.06

 * Eur. J. Org. Chem. 2016, , 4050-4058
10.1002/ejoc.201600572
diarylallylium ion (3-F)2
*

E Param.: 4.15

 ** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
indolecarboxylate derived iminium ion
*
 dichloromethane

E Param.: -9.50

 ** Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(tfm)2CH+
C15H9F6 *

E Param.: 7.96

 ** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(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)-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)-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-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-(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-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
(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-((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
(2S,5S)-5-benzyl-3-methyl-4-oxo-1-(3-phenylallylidene)-2-((E)-styryl)imidazolidin-1-ium
C28H27N2O *
 dichloromethane

E Param.: -5.90

 ** Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009