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

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Abstract

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
Volume84
Issue number2
DOIs
Publication statusPublished - Aug 5 2001

Fingerprint

Molecular modeling
assemblies
Dimers
acids
Acids
dimers
ribbons
attachment
Hydrogen bonds
Agglomeration
methylidyne
hydrogen bonds
Derivatives
configurations
interactions
energy

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

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abstract = "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.",
keywords = "α-pyridyl- and α-furylcinnamic acids, Intermolecular hydrogen-bonded network, Molecular modeling, Semiempirical methods",
author = "I. P{\'a}link{\'o} and T. K{\"o}rtv{\'e}lyesi",
year = "2001",
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T1 - Structural motifs in α-pyridyl- and α-furylcinnamic acid assemblies-a molecular modeling study

AU - Pálinkó, I.

AU - Körtvélyesi, T.

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Y1 - 2001/8/5

N2 - 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.

AB - 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.

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KW - Semiempirical methods

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