Structural motifs in α-pyridyl- and α-furylcinnamic acid assemblies-a molecular modeling study

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8 Citations (Scopus)


The aggregation properties of stereoisomeric 2-(3′-furyl)-3-phenylpropenoic acids (FU3E, FU3Z, α-furylcinnamic acids) and 2-(4′-pyridyl)-3-phenylpropenoic acids (PY4E, PY4Z, α-pyridylcinnamic acids) were studied by the PM3 semiempirical quantum chemical method. Calculations revealed that (aromatic)C-H...N(O) hydrogen bonds made possible the attachment of dimer units; thus, virtually infinite chains can be built out of FU3Z, PY4E, and PY4Z. The energy-minimized structure had zig-zag configuration. PY4Z dimers allowed the formation of ribbonlike network; however, the number of structural units could not be increased infinitely. One of the furyl derivatives (FU3E) could not be stabilized either in the ribbon or the chain form; however, (aromatic)CH...π or (aromatic)π...(aromatic)π interactions contribute to the packing pattern of the two dimers.

Original languageEnglish
Pages (from-to)269-275
Number of pages7
JournalInternational Journal of Quantum Chemistry
Issue number2
Publication statusPublished - Aug 5 2001
Event3th European Conference on Computational Chemistry (EUCO-CC3) - Budapest, Hungary
Duration: Sep 4 2000Sep 8 2000


  • Intermolecular hydrogen-bonded network
  • Molecular modeling
  • Semiempirical methods
  • α-pyridyl- and α-furylcinnamic acids

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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