Electrochemical reduction of 2,4-dimethyl(diethyl)-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium hexafluorophosphates and 2,4-dimethyl(diethyl)-9H-thioxanthene-9-ones

Leonid A. Shundrin, Pavel A. Avrorov, Irina G. Irtegova, Danila S. Odintsov, Alexander F. Poveshchenko

Research output: Contribution to journalArticlepeer-review

Abstract

Electrochemical reduction of 2,4-dimethyl(diethyl)-9-oxo-10-(4-heptoxyphenyl)-9H-thioxanthenium hexafluorophosphates in acetonitrile (MeCN) and N,N-dimethylformamide is an irreversible 1-electron process accompanied by the cleavage of the C(Ph)-S bond in thioxanthenium cations with the formation of the corresponding 2,4-dimethyl(diethyl)-9H-thioxanthene-9-ones. One-electron reversible electrochemical reduction of the latter compounds occurs at more negative potentials and yields the corresponding radical anions, which have been characterized by electron paramagnetic resonance spectroscopy and density functional theory calculations at the (U)B3LYP/6-31+G*/polarizable continuum model level of theory.

Original languageEnglish
Article number3853
Number of pages7
JournalJournal of Physical Organic Chemistry
Volume31
Issue number9
DOIs
Publication statusPublished - 1 Sep 2018

Keywords

  • Cyclic voltammetry
  • DFT calculations
  • EPR spectroscopy
  • Radical anions
  • Thioxanthenium salts
  • Thioxanthenones
  • thioxanthenones
  • cyclic voltammetry
  • radical anions
  • thioxanthenium salts
  • ELECTRON
  • THIOXANTHONE
  • SULFONIUM SALTS
  • DERIVATIVES

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