Molecular ions of 3,3′-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1′-dioxides

L. A. Shundrin, I. G. Irtegova, A. D. Rogachev, V. A. Reznikov

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The electrochemical reduction of 3,3′-bi(2-R-5,5-dimethyl-4- oxopyrrolinylidene) 1,1′-dioxides (R = CF3, Me, Ph, Bu t), which are cyclic dinitrons with conjugated C=C bond, in acetonitrile is an EE process producing stable radical anions and dianions, whereas the electrochemical oxidation is an EEC (R = Me, Ph) or EE process (R = But) with formation of radical cations (except for the case of R = CF3) and dications (R = But) stable under standard conditions. Radical cations of the dioxides with R = Me, Ph, and But and radical anions of the whole series of the compounds studied, including R = CF3, were characterized by ESR spectroscopy combined with electrochemical measurements and quantum-chemical calculations. The electrochemical behavior of the But-substituted dinitron is unique: the EE processes in the region of negative and positive potentials with formation of the dianion, radical anion, radical cation, and dication stable at T = 298 K were observed for the first time within one cycle of potential sweep in the CV curve measured in MeCN.

Original languageEnglish
Pages (from-to)1178-1184
Number of pages7
JournalRussian Chemical Bulletin
Volume54
Issue number5
DOIs
Publication statusPublished - May 2005
Externally publishedYes

Keywords

  • 3,3′-bi(2-r-5,5-dimethyl-4-oxopyrrolinylidene) 1,1′-dioxides
  • Cyclic nitrons
  • Cyclic voltammetry
  • Dianions
  • Dications
  • Electrooxidation
  • Electroreduction
  • ESR spectroscopy
  • Radical anions
  • Radical cations

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