Toward Hexaphenylethane: Structure and Decomposition of Crystalline Triphenylmethyl Iodide

C. Richard Arkin, Brett Cowans, Bart Kahr

Research output: Contribution to journalArticle

Abstract

Triphenylmethyl iodide (C19H15I) crystallizes in the monoclinic system: a = 15.919(6) Å, b = 10.826(6) Å, c = 19.397(11) Å, β = 114.86(4)°, space group C2/c, Z = 8. In the structure, heterochiral propeller molecules are interdigitated. This arrangement, coupled with earlier reports of the thermal instability of triphenylmethyl iodide, suggested a convenient, topochemically controlled, solid-state synthesis of the elusive hydrocarbon hexaphenylethane. Crystals of the 13Cmethyl-labeled triphenylmethyl iodide were heated to 100 °C in a rotor spinning at the magic angle within an NMR spectrometer. Spectral changes and accompanying analyses by plasma desorption mass spectrometry, calorimetry, and ESR spectroscopy reveal that the major product in the decomposition is triphenylmethane, produced by hydrogen atom abstractions from neighboring triphenylmethyl radicals, that subsequently oligomerize. These data provide a new view of the thermal stability of triphenylmethyl iodide in the solid state and an old view of the accessibility of hexaphenylethane.

Original languageEnglish (US)
Pages (from-to)1500-1503
Number of pages4
JournalChemistry of Materials
Volume8
Issue number7
DOIs
StatePublished - Jul 1996

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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