Evidence for a π dimer in the electrochemical reduction of 1,3,5-trinitrobenzene: A reversible N<inf>2</inf>-fixation system

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Abstract

(Figure Presented) Electrochemical reduction of 1,3,5-trinitrobenzene (1) forms π dimer 2, which evolves to a more stable ω complex. The crystal structure of the NEt4+ salt of 2 shows π-stacked chains of radical anions. Solid 2 or dimeric 2 in solution reacts with N2 to give a dianion in which an azo group links two 1,3,5-trinitrobenzene units (see picture). The azo derivative is reversibly electrochemically oxidized to 1. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Original languageEnglish
Pages (from-to)1321-1325
JournalAngewandte Chemie - International Edition
Volume46
Issue number8
DOIs
Publication statusPublished - 2 Jul 2007

Keywords

  • Azo compounds
  • Electrochemistry
  • Nitrogen fixation
  • Radicals
  • Stacking interactions

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