Structural motifs in α‐pyridyl‐ and α‐furylcinnamic acid assemblies— A molecular modeling study

Abstract

AbstractThe 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. © 2001 John Wiley & Sons, Inc. Int J Quantum Chem 84: 269–275, 2001