Hydrogen bonding interactions in E- or Z-2-phenyl-3-(X′-pyridyl)propenoic acid (X=2, 3 or 4) assemblies - A molecular modeling study

József Csehi, István Pálinkó

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The agglomeration properties of stereoisomeric 2-phenyl-3-(X′-pyridyl)propenoic acids (X=2, 3 or 4) were studied by the PM3 semiempirical quantum chemical method. Calculations revealed that dimers kept together by the intermolecular hydrogen bonding interactions of the carboxylic groups could be built from both stereoisomers irrespective of the position of the nitrogen heteroatom. The dimers of the Z-isomers could also be built through (aromatic C-H...N hydrogen bonds between the dimer units. The longest agglomerate was the pentamer of the dimers when the nitrogen was in the 2′ position. Longer hydrogen-bonded agglomerates than dimers could only be constructed from the E-isomer with the nitrogen in position 4′. Here, the trimer of the dimers proved to be the longest hydrogen-bonded entity and similarly to the Z-isomers, the dimer units are kept together by (aromatic)C-H...N intermolecular hydrogen bonds.

Original languageEnglish
Pages (from-to)151-154
Number of pages4
JournalJournal of Molecular Modeling
Volume10
Issue number2
DOIs
Publication statusPublished - Apr 1 2004

Keywords

  • 2-phenyl-3-(X′-pyridyl)propenoic acids (X=2, 3 or 4)
  • Intermolecular hydrogen bonded network
  • Semiempirical method

ASJC Scopus subject areas

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry

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