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 | | 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 | | 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 | | 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 | | 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 | | 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 | |
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 |
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 |
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 |
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 |
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 |
E Param.: -4.96 | | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
2-(4-methoxyphenyl)chromenylium ion |
E Param.: -4.95 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(dpa)2CH+ |
E Param.: -4.72 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium |
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+ |
E Param.: -3.85 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tropylium ion |
E Param.: -3.72 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
flavylium ion |
E Param.: -3.45 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(pfa)2CH+ |
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 |
E Param.: -3.02 | | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
1,1-dianisyl-3-phenylallylium ion |
E Param.: -2.67 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion |
E Param.: -2.19 | | J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298 | |
1,3-dithianylium ion |
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 |
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+ |
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 |
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+ |
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 |
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+) |
E Param.: 0.51 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
ani(pop)CH+ |
E Param.: 0.61 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
9-(4-methoxyphenyl)-9H-fluoren-9-ylium |
dichloromethane | E Param.: 0.85 | | Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963 |
1,1,3-triphenylallylium ion |
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+ |
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 |
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 |