Mayr's Database of Reactivity Parameters

Carbocations

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(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
pop(tol)CH+
C20H17O *

E Param.: 2.16, Deviation: ±0.03

*** 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
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
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
(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
MacMillan-iminium ion (1st generation)
C22H25N2O+ *
MeCN

E Param.: -7.37

*** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
mor iminium
C13H16NO+ *

E Param.: -8.60

*** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
cumyl cation
*

E Param.: 5.74

*** Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
diarylallylium ion (3,3-F2)2
*

E Param.: 6.11

*** 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
diphenylallylium ion
*

E Param.: 2.70

*** 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-p-anisyl-allylium ion
*

E Param.: -1.45

*** 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
bis(julidin-9-yl)allylium ion
*

E Param.: -9.78

*** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
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
PhCH=N+Me2 (in MeCN)
C9H12N *
MeCN

E Param.: -9.27

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
pTolCH=N+CH2 (in MeCN)
C10H14N *
MeCN

E Param.: -9.64

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
p-AniCH=N+Me2 (in MeCN)
C10H14NO *
MeCN

E Param.: -10.69

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)4 (in MeCN)
C11H14N *
MeCN

E Param.: -9.35

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)5 (in MeCN)
C12H16N *
MeCN

E Param.: -9.60

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
p-CF3-C6H4-CH=N+Me2 (in MeCN)
C10H11F3N *
MeCN

E Param.: -8.34

*** J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
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
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