Molecular Orbital Effects on the Structure of Cyclopropane Radical Cations

Heinz D. Roth, Marcia L.M. Schilling, Frederic C. Schilling

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

The interaction of photoexcited electron acceptors with selected cyclopropane derivatives results in electron transfer and generates radical ion pairs. Nuclear spin-polarization effects observed during these reactions allow an insight into the structures of the intermediates. The radical cations can assume two different structure types, which are derived either from the 2A1 or the 2B2 cyclopropane radical cation. Spiro [cyclopropane-1,9'-fluorene] gives rise to a radical cation, 12, in which two cyclopropane bonds are weakened (2B2). In contrast, 2,3-benzo-5,6-cyclopropanorbornene has a radical cation, 16, in which a single cyclopropane bond is weakened (2A1). These structures can be rationalized on the basis of frontier molecular orbital considerations.

Original languageEnglish (US)
Pages (from-to)4152-4158
Number of pages7
JournalJournal of the American Chemical Society
Volume107
Issue number14
DOIs
StatePublished - Jul 1985
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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