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

摘要

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. (C) 2001 John Wiley & Sons, Inc. [References: 10]