Hydrogen bonding interactions of α-phenylcinnamic acid isomers in the liquid phase studied by IR and NMR spectroscopies and computational methods

I. Pálinkó, B. Török, M. Rózsa-Tarjányi, J. T. Kiss, Gy Tasi

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Abstract

Intra- and intermolecular hydrogen bonding interactions of α-phenylcinnamic acid isomers were studied in the solution phase by infrared (IR) and proton nuclear magnetic resonance (1H NMR) spectroscopies and the AM1 semi-empirical method. The solvents were CDCl3 or dimethyl sulfoxide (DMSO), the concentration of the acid isomers were varied. Spectroscopic measurements revealed that (i) intermolecular hydrogen bonds are typical for both acid isomers via their carboxylic groups (OH…O hydrogen bonding), monomer acids were only present in significant amounts at 10−4 mol/dm3 and (ii) CDCl3 was not involved in the aggregated structures of any isomers, while the oxygen in DMSO seemed to interact with the olefinic proton of the E isomer. Weak intramolecular hydrogen bonds could be identified computationally in the Z isomer: (aromatic)CH…O, CO…H, but none in the E.

Original languageEnglish
Pages (from-to)57-60
Number of pages4
JournalJournal of Molecular Structure
Volume348
DOIs
Publication statusPublished - Jan 1 1995

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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