Aromaticity of Highly Bent Benzene Rings. An Investigation by High Field Deuterium NMR of [5]Metacyclophane and Model Compounds

P. C.M. van Zijl, L. W. Jenneskens, E. W. Bastiaan, C. MacLean, W. H. de Wolf, F. Bickelhaupt

Research output: Contribution to journalArticle

Abstract

High field deuterium NMR provides a new and simple method for establishing the degree of aromaticity of a compound. The procedure is based on the determination of the magnetic susceptibility anisotropy from quadrupolar deuterium couplings of molecules in solution aligned by the magnetic field. The technique is illustrated for some deuterated dialkylbenzenes (2d, 3e, 4e) and applied to [8,11-2H2][5]metacyclophane (1d). Surprisingly, 1d is found to be fully aromatic in spite of its strongly bent benzene ring.

Original languageEnglish (US)
Pages (from-to)1415-1418
Number of pages4
JournalJournal of the American Chemical Society
Volume108
Issue number7
DOIs
StatePublished - Jan 1 1986
Externally publishedYes

ASJC Scopus subject areas

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

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