Conformations of 2-phenyl-3-pyridylpropenoic acid (alpha-phenyl pyridylcinnamic acid) dimers – A computational study

Pálinkó, István (2005) Conformations of 2-phenyl-3-pyridylpropenoic acid (alpha-phenyl pyridylcinnamic acid) dimers – A computational study. INTERNET ELECTRONIC JOURNAL OF MOLECULAR DESIGN, 4 (8). pp. 537-544. ISSN 1538-6414

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Abstract

Motivation. Cinnamic acid analogs are not only important parts of the shikimic acid metabolic pathway of higher plants but it is possible to assemble, particularly from those containing oxygen or nitrogen heteroatoms, various patterned structures kept together with CH...O or CH...N hydrogen bonds. The fundamental unit of these structures is the acid dimer, e.g., the dimer of E and Z–2–phenyl–3–pyridylpropenoic acids of this study, which may exist in many conformations. As a preparation for a detailed conformational analysis of the patterned structures, it was decided to study the conformational behavior of these acid dimers, containing the N heteroatom in all possible positions of the aromatic ring. The conformational behavior of any cinnamic acid analogs in the dimeric form has not been studied before. Method. The conformational search module of the HyperChem package was used for the conformational analysis of the acid dimers with the PM3 semiempirical method. Calculations were performed for isolated dimers, i.e., without solvent. Results. The conformational search identified many conformers of the acid dimers. Although their numbers amounted to hundreds, they were found to fill the conformational space unevenly, in a highly symmetric nature. The distribution patterns were typical for the stereoisomers, but resembled to each other irrespective to the position of the nitrogen atom. Conclusions. It was proved to be possible to study the conformational behavior of cinnamic acid analogs in their dimeric forms for the first time. Large number of conformers was identified and they were found the fill the conformational space in a patterned way.

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