Mayr's Database of Reactivity Parameters

Carbocations

« Back Forward » Found 132 molecules, displaying page 1 of 1 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
p-AniCH=N+Me2 (in MeCN)
C10H14NO*
MeCN

E Param.: -10.69

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
(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
pipN+=CH-CH-Ph
C14H18N+*

E Param.: -10.30

*Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
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
(lil)2CH+
C23H25N2*

E Param.: -10.04

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion
C27H32N3*

E Param.: -9.84

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
pyrN+=CH-CH-Ph
C13H16N+*

E Param.: -9.80

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
bis(julidin-9-yl)allylium ion
*

E Param.: -9.78

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
pTolCH=N+CH2 (in MeCN)
C10H14N*
MeCN

E Param.: -9.64

***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
indolecarboxylate derived iminium ion
*
dichloromethane

E Param.: -9.50

**Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(jul)2CH+
C25H29N2*

E Param.: -9.45

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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+Me2 (in MeCN)
C9H12N*
MeCN

E Param.: -9.27

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
Me2N+=CH-CH-Ph
C11H14N+*

E Param.: -9.20

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion
*

E Param.: -8.97

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(ind)2CH+
C19H21N2*

E Param.: -8.76

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
mor iminium
C13H16NO+*

E Param.: -8.60

***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
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
(thq)2CH+
C21H25N2*

E Param.: -8.22

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
Jorgensen/Hayashi-iminium ion
C29H34NOSi+*

E Param.: -8.20

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(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
(4-NMe2)-tritylium ion
*

E Param.: -7.93

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
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
(pyr)2CH+
C21H25N2*

E Param.: -7.69

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
MacMillan-iminium ion (spiro)
*
MeCN

E Param.: -7.67

***Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
diarylallylium ion (4-NMe2)2
*

E Param.: -7.50

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
MacMillan-iminium ion (1st generation)
C22H25N2O+*
MeCN

E Param.: -7.37

***Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
(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-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
N-methylacridinium ion
C14H12N*

E Param.: -7.15

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(dma)2CH+
C17H21N2*

E Param.: -7.02

*****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
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
dimethylmethyleneammonium ion
C3H8N*

E Param.: -6.69

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

E Param.: -6.43

***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
(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)-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-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
bis(1-methylindol-3-yl)methylium ion
C19H17N2*

E Param.: -5.99

***J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
2-phenyl-1,3-dithiolan-2-ylium ion
C9H9S2*

E Param.: -5.91

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(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
(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
(mpa)2CH+
C27H25N2*

E Param.: -5.89

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
Vilsmeier ion
C3H7ClN*

E Param.: -5.77

*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(mor)2CH+
C21H25N2O2*

E Param.: -5.53

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
MacMillan-iminium ion (2nd generation)
*
MeCN

E Param.: -5.52

***Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
methyl(phenyl)methyleneammonium ion
C8H10N*

E Param.: -5.17

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

E Param.: -4.95

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(dpa)2CH+
C37H29N2*

E Param.: -4.72

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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
(4-MeO)3-tritylium ion
*

E Param.: -4.35

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(mfa)2CH+
C19H19F6N2*

E Param.: -3.85

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tropylium ion
C7H7*

E Param.: -3.72

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
flavylium ion
C15H11O*

E Param.: -3.45

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(pfa)2CH+
C29H23F6N2*

E Param.: -3.14

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(4-MeO)2-tritylium ion
*

E Param.: -3.04

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
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
1,1-dianisyl-3-phenylallylium ion
C23H21O2*

E Param.: -2.67

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

E Param.: -2.14

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(4-MeO,4-Me)-tritylium ion
*

E Param.: -2.13

-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
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
(4-MeO,3-OMe)-tritylium ion
*

E Param.: -1.62

-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
di-p-anisyl-allylium ion
*

E Param.: -1.45

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
(fur)2CH+
C17H15O2*

E Param.: -1.36

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(4-Me)3-tritylium ion
*

E Param.: -1.21

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(fur)(ani)CH+
*

E Param.: -0.81

*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(4-Me)2-tritylium ion
*

E Param.: -0.70

-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[...]
(4-Me)-tritylium ion
*

E Param.: -0.13

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(ani)2CH+
C15H15O2*

E Param.: 0.00

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(4-F)3-tritylium ion
*

E Param.: 0.05

*Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
methoxy-(4-methoxyphenyl)methylium ion
C9H11O2*

E Param.: 0.14

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(4-F)2-tritylium ion
*

E Param.: 0.17

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

E Param.: 0.35

*Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
tritylium ion (Ph3C+)
C19H15*

E Param.: 0.51

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ani(pop)CH+
C20H17O2*

E Param.: 0.61

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
9-(4-methoxyphenyl)-9H-fluoren-9-ylium
C20H27O*
dichloromethane

E Param.: 0.85

***Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
1,1,3-triphenylallylium ion
C21H17*

E Param.: 0.98

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(3-F)-tritylium ion
*

E Param.: 1.01

*Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(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
di-p-tolyl-allylium ion
*

E Param.: 1.23

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
(4-CF3)-tritylium ion
*

E Param.: 1.33

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ani(tol)CH+
C15H15O*

E Param.: 1.48

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(3-F)2-tritylium ion
*

E Param.: 1.54

*Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
methoxy-(4-methylphenyl)methylium ion
C9H11O*

E Param.: 1.90

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(3-Cl)3-tritylium ion
*

E Param.: 1.99

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

E Param.: 2.07

*Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
ani(Ph)CH+
C14H13O*

E Param.: 2.11

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
pop(tol)CH+
C20H17O*

E Param.: 2.16

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(4-CF3)2-tritylium ion
*

E Param.: 2.28

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
N-ethylidenecarbazolium ion
C14H12N*

E Param.: 2.41

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
9-phenyl-9H-fluoren-9-ylium
C19H25*
dichloromethane

E Param.: 2.41

***Chem. Eur. J. 2017, 23, 623-630
10.1002/chem.201603963
(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
diphenylallylium ion
*

E Param.: 2.70

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

E Param.: 2.89

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
pop(Ph)CH+
C19H15O*

E Param.: 2.90

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
methoxy-phenylmethylium ion
C8H9O*

E Param.: 2.97

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

E Param.: 3.20

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(tol)2CH+
C15H15*

E Param.: 3.63

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
diarylallylium ion (3-F)2
*

E Param.: 4.15

**J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
tol(Ph)CH+
C14H13*

E Param.: 4.43

*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(pfp)2CH+
C13H9F2*

E Param.: 5.01

*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
pfp(Ph)CH+
C13H10F*

E Param.: 5.20

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

E Param.: 5.24

*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
benzhydrylium ion Ph2CH+
C13H11*

E Param.: 5.47

*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(pcp)2CH+
C13H9Cl2*

E Param.: 5.48

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

E Param.: 5.74

***Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
(2,4,6-trimethylphenyl)ethylium ion
C11H15*

E Param.: 6.04

*Macromolecules 2005, 38, 33-40
10.1021/ma048389o
diarylallylium ion (3,3-F2)2
*

E Param.: 6.11

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion
C22H29*

E Param.: 6.16

*Macromolecules 2005, 38, 33-40
10.1021/ma048389o
(mfp)PhCH+
*

E Param.: 6.23

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

E Param.: 6.70

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

E Param.: 6.74

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

E Param.: 6.87

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

E Param.: 7.52

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

E Param.: 7.96

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

E Param.: 8.02

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