Aromaticity of the completely annelated tetraphenylenes: NICS and GIMIC characterization

Gleb V. Baryshnikov, Nataliya N. Karaush, Rashid R. Valiev, Boris F. Minaev

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A series of heterocyclic and hydrocarbon [8]circulenes (also named completely annelated tetraphenylenes) were studied by the NICS and GIMIC methods in order to describe their aromatic properties from the magnetic criterion point of view. According to calculations all the hetero[8]circulene molecules demonstrate the bifacial aromatic/antiaromatic nature. The inner octatetraene core of the studied [8]circulenes is characterized by the presence of paratropic (“antiaromatic”) ring currents, whereas the outer macrocycle constructed from the five- and six-membered rings possesses the magnetically-induced diatropic (“aromatic”) ring current. The hydrocarbon [8]circulenes studied in this work consist of a similar planar cyclooctatetraene core but they exhibit a rather different balance of magnetically-induced ring currents.

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Original languageEnglish
JournalJournal of Molecular Modeling
Volume21
Issue number6
DOIs
Publication statusPublished - 1 Jun 2015

Keywords

  • Antiaromaticity
  • Aromaticity
  • Gauge-including atomic orbitals
  • Hetero[8]circulenes
  • NICS indices
  • Octatetraene ring
  • Tetraphenylenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computer Science Applications
  • Computational Theory and Mathematics
  • Catalysis
  • Organic Chemistry
  • Inorganic Chemistry

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