E-2-benzylidenebenzocycloalkanones. Stereostructure and NMR spectroscopic investigation

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28 Citations (Scopus)


Series of E-2-benzylideneindanones (a), -tetralones (b) and - benzosuberones (c) with OCH3 (2-4), NO2 (5-7) and F (8-10) substitutions (ortho, meta and para) on their benzylidene moiety were synthesized by aldol condensation of the appropriate aldehydes and benzocyclanones. The stereostructure (configuration and conformation) and the electronic properties (conjugation of the enone moiety with the aromatic rings) of the compounds were studied by IR, 1H and 13C NMR spectroscopy including also 2D-HSC, DNOE and DEPT measurements. Ab initio calculations were carried out to corroborate the experimental findings.

Original languageEnglish
Pages (from-to)13-19
Number of pages7
JournalJournal of Molecular Structure
Issue number1
Publication statusPublished - Apr 13 1999


  • Ab initio geometry optimisation
  • E-2-benzylideneindanones -tetralones - benzosuberones
  • IR, H and C NMR spectra
  • Stereostructure

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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