Ring Currents in Benzo- and Benzocyclobutadieno-Annelated Biphenylene Derivatives

Slavko Radenkovic*, Jelena Tosovic, Remco W. A. Havenith, Patrick Bultinck

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

10 Citations (Scopus)

Abstract

The effect of benzo and benzocyclobutadieno annelation on the current density induced in a series of biphenylene derivatives is examined at the B3LYP/cc-pVDZ level of theory, by using the CTOCD-DZ method. Angular benzo annelation increases, whereas linear benzo annelation decreases the intensity of paratropic (antiaromatic) current density along the four-membered ring of biphenylene. The opposite effect is found for benzocyclobutadieno annelation. It is shown that the extent of local aromaticity of the four-membered ring in biphenylene congeners can vary from highly antiaromatic to nonaromatic, as a result of different modes of annelation.

Original languageEnglish
Pages (from-to)216-222
Number of pages7
JournalChemphyschem
Volume16
Issue number1
DOIs
Publication statusPublished - 12-Jan-2015

Keywords

  • aromaticity
  • density functional calculations
  • hydrocarbons
  • magnetic properties
  • polycycles
  • MOLECULAR MAGNETIC-PROPERTIES
  • CURRENT-DENSITY
  • CYCLIC CONJUGATION
  • CHEMICAL-SHIFTS
  • PCP-RULE
  • AROMATICITY
  • HYDROCARBONS
  • ELECTRON
  • SYSTEMS
  • PHENYLENES

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