Mayr's Database of Reactivity Parameters

N-substituted carbocations (iminium ions)

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
dimethylmethyleneammonium ion
C3H8N *

E Param.: -6.69

* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methyl(phenyl)methyleneammonium ion
C8H10N *

E Param.: -5.17

* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
Vilsmeier ion
C3H7ClN *

E Param.: -5.77

* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
pipN+=CH-CH-Ph
C14H18N+ *

E Param.: -10.30

* Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
indolecarboxylate derived iminium ion
*
dichloromethane

E Param.: -9.50

** Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(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)-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
(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
(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
(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