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

Pálinkó, István and Körtvélyesi, Tamás (2001) Structural motifs in alpha-pyridyl- and alpha-furylcinnamic acid assemblies - a molecular modeling study. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 84 (2). pp. 269-275. ISSN 0020-7608

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Abstract

The aggregation properties of stereoisomeric 2-(3 ' -furyl)-3-phenylpropenoic acids (FUSE, FU3Z, alpha -furylcinnamic acids) and 2-(4 ' -pyridyl)-3-phenylpropenoic acids (PY4E, PY4Z, alpha -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 (FUSE) could not be stabilized either in the ribbon or the chain form; however, (aromatic)CH...pi or (aromatic)pi...(aromatic)pi interactions contribute to the packing pattern of the two dimers.

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