Aromaticity and Optical Activity

Veronica L. Murphy, Adam Reyes, Bart Kahr

Research output: Contribution to journalArticle

Abstract

The relationship between aromaticity and optical activity is investigated in comparisons of heterocycles with 4n + 2 and 4n π-electrons, in cyclic ketones with and without aromatic resonance structure representations, in tautomers and pericyclic reaction partners in which only one compound of each pair is aromatic, and in partially hydrogenated cyclo-C18 derivatives with both radial and tangential π-orbitals. In all comparisons, aromaticity is correlated to diminished optical activity. A heuristic explanation of this observation is grounded in the electric dipole-magnetic dipole polarizability contribution to optical activity in which the sense of electric dipoles and magnetic dipoles become uncoupled when electrons can circulate around a ring with either sense. These observations form a basis for making broad structure-optical activity correlations from inspection of molecular structure.

Original languageEnglish (US)
Pages (from-to)25-27
Number of pages3
JournalJournal of the American Chemical Society
Volume138
Issue number1
DOIs
StatePublished - Jan 13 2016

ASJC Scopus subject areas

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

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