Cyclic conjugation effects in cyclacenes

Ivan Gutman*, P. Ulrich Biedermann, Vesna Ivanov-Petrović, Israel Agranat

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

Cyclic conjugation is studied in Hückel and Möbius cyclacenes as well as in a few other related open-chain and cyclic belt-shaped hydrocarbons (e.g., zig-zag cyclarenes). The main conclusions are that (a) the energy effect of the conjugation along the perimeter of cyclacenes is relatively large, (b) conjugation along the 6 -, 10 - and 14-membered cycles has a much greater effect, in spite of the fact that these cycles embrace bonds that formally are not involved in cyclic conjugation. Möbius cyclacenes are non-alternant hydrocarbons and their odd-cycles have a significant contribution to conjugation. The contribution of conjugation in individual cycles to the total resonance energy is briefly discussed.

Original languageEnglish
Pages (from-to)189-202
Number of pages14
JournalPolycyclic Aromatic Compounds
Volume8
Issue number2-3
DOIs
StatePublished - 1996

Keywords

  • Belt-shaped conjugated hydrocarbons
  • Cyclacenes
  • Cyclic conjugation
  • Cyclopolyacenes
  • Hückel
  • Möbius
  • Topological resonance energy
  • Topology
  • Zig-zag cyclarenes

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