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, I. Pálinkó

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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 2004

Fingerprint

Molecular modeling
Hydrogen Bonding
Dimers
assemblies
Hydrogen
Hydrogen bonds
dimers
acids
Acids
Nitrogen
hydrogen
Isomers
interactions
isomers
Stereoisomerism
nitrogen
hydrogen bonds
trimers
agglomeration
acrylic acid

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biophysics
  • Computer Science Applications
  • Computational Theory and Mathematics

Cite this

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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.",
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AU - Pálinkó, I.

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N2 - 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.

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