Article,

Electronic stabilization through 7-p electron conjugation in heterocycles. Molecular and crystal structure of an inert monocyclic radical cation

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Chemische Berichte, 121 (11): 2059--2061 (1988)

Abstract

The 1,4-diethylpyrazinium (I) and -quinoxalinium cation radicals are more stable than methylviologen and phenazinium radical cations and do not show assocn. in concd. soln. or in the solid, as demonstrated by ESR and by a crystal structure anal. of I.BPh4-. Isolation of these unusually stable radical ions has been accomplished for the first time. Their persistence stands in contrast to conventional conceptions of radical stabilization which involve either steric shielding or extensive p electron delocalization over many p centers. on SciFinder(R)

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