Hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives studied by FT-IR spectroscopy and calculations

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Abstract

Intermolecular hydrogen bonding interactions in stereoisomeric α-substituted cinnamic acid methyl esters (methyl 2,3-diphenylpropenoate, methyl 2-phenyl-3-(2′-methoxyphenyl)-propenoate, methyl 2-(2′-methoxyphenyl)-3-phenylpropenoate and methyl-2,3-bis(2′-methoxyphenyl)-propenoate) were studied by FT-IR spectroscopy and model calculations at the semi-empirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H . . . O types were found to be general in the solid state, but rare in solution. In this hydrogen bond the carbon may be part of either aromatic ring or the olefinic bond. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). Pointing out differences between the stereoisomers was also possible.

Original languageEnglish
Pages (from-to)63-73
Number of pages11
JournalVibrational Spectroscopy
Volume22
Issue number1-2
DOIs
Publication statusPublished - Jan 1 2000
EventThe 17th Australian-Hungarian International Conference on Vibrational Spectroscopy - Balatonfured, Hungary
Duration: Apr 7 1999Apr 9 1999

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Keywords

  • FT-IR spectroscopy
  • Intermolecular hydrogen bonds
  • Semi-empirical quantum chemical calculations (the PM3 method)
  • Stereoisomeric α-substituted cinnamic acid methyl esters

ASJC Scopus subject areas

  • Spectroscopy

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