Mayr's Database of Reactivity Parameters

N-substituted carbocations (iminium ions)

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
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
pyrN+=CH-CH-Ph
C13H16N+ *

E Param.: -9.80

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