The aromaticity of benzene and the lack of aromaticity of cyclooctatetraene: Is our calorimetric perspective a manifestation of convenience, anthropocentrism or folksonomy?

Kathleen F Kay Edwards, Stefan Perişanu, Joel F. Liebman

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

The aromaticity of benzene and its lack in cyclooctatetraene were analyzed by several methods: simple and two-carbon group additivity, experimental realization of the Dewar-Breslow definition of aromaticity, enthalpies of hydrogenation of different kinds of unsaturated hydrocarbons. All calculations showed a large difference in the stabilization energies of the two molecules, which confirms that benzene is aromatic, while cyclooctatetraene is not. Comments about terms of anthropocentric origin used for the derivatives of benzene are made, as are discussions of convenience and folksonomy.

Original languageEnglish (US)
Title of host publicationAdvances in Chemical Modeling
PublisherNova Science Publishers, Inc.
Pages417-431
Number of pages15
Volume5
ISBN (Print)9781634823111, 9781634823104
StatePublished - Apr 1 2015
Externally publishedYes

Keywords

  • Anthropocentrism
  • Aromaticity
  • Benzene
  • Cyclooctatetraene
  • Folksonomy
  • Group increments
  • Stabilization

ASJC Scopus subject areas

  • Chemistry(all)

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