Carbocations
| 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)  |
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  |
dichloromethane | E Param.: -10.60 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
pipN+=CH-CH-Ph  |
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  |
E Param.: -10.23 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
(lil)2CH+  |
E Param.: -10.04 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion  |
E Param.: -9.84, Deviation: ±0.21 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
pyrN+=CH-CH-Ph  |
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)  |
MeCN | E Param.: -9.64 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
PhCH=N+(CH2)5 (in MeCN)  |
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+  |
E Param.: -9.45 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
PhCH=N+(CH2)4 (in MeCN)  |
MeCN | E Param.: -9.35 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
PhCH=N+Me2 (in MeCN)  |
MeCN | E Param.: -9.27 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
Me2N+=CH-CH-Ph  |
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, Deviation: ±0.32 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(ind)2CH+  |
E Param.: -8.76 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
mor iminium  |
E Param.: -8.60 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
(PhCH2)2N+=CH-CH-Ph  |
E Param.: -8.50 |
|
Angew. Chem. Int. Ed. 2008, 47, 8723-8726 10.1002/anie.200802889 |
|
p-CF3-C6H4-CH=N+Me2 (in MeCN)  |
MeCN | E Param.: -8.34 |
|
J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
(thq)2CH+  |
E Param.: -8.22 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
Jorgensen/Hayashi-iminium ion  |
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  |
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  |
E Param.: -7.79 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
(pyr)2CH+  |
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)  |
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  |
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  |
dichloromethane | E Param.: -7.20 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
N-methylacridinium ion  |
E Param.: -7.15, Deviation: ±0.12 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(dma)2CH+  |
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  |
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  |
E Param.: -6.90 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
dimethylmethyleneammonium ion  |
E Param.: -6.69 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
2-phenyl-1,3-dithianylium ion  |
E Param.: -6.43, Deviation: ±0.04 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
3-(4-(dimethylamino)benzylidene)-1-methyl-3H-indol-1-ium ion  |
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  |
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  |
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  |
dichloromethane | E Param.: -6.00 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
bis(1-methylindol-3-yl)methylium ion  |
E Param.: -5.99 |
|
J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 |
|
2-phenyl-1,3-dithiolan-2-ylium ion  |
E Param.: -5.91, Deviation: ±0.33 |
|
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  |
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  |
dichloromethane | E Param.: -5.90 |
|
Asian J. Org. Chem. 2014, 3, 550-555 10.1002/ajoc.201402009 |
(mpa)2CH+  |
E Param.: -5.89 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
|
Vilsmeier ion  |
E Param.: -5.77 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
|
(mor)2CH+  |
E Param.: -5.53 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |