Intermolecular hydrogen bonding interactions between a-phenyl furylcinnamic acid stereoisomers studied by semiempirical quantum chemical method

Talabér, E. and Paksi, Z. and Pálinkó, István (2003) Intermolecular hydrogen bonding interactions between a-phenyl furylcinnamic acid stereoisomers studied by semiempirical quantum chemical method. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 620 (1). pp. 37-41. ISSN 0166-1280

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Abstract

The possibilities of intermolecular hydrogen bonding interactions were studied between 2-phenyl-3(2'-furyl)propenoic acid and 2-phenyl-3(3'-furyl)propenoic acid stereoisomers (alpha-phenyl furylcinnamic acids) by semiempirical quantum chemical method. Calculations revealed that long-range ordering was only possible between the hydrogen-bonded, dimers of the Z isomers. Then, the chain-like structures were held together by (phenyl)C-H ... (furyl)0 close contacts. However, the chain length could not be increased infinitely, it was limited to the pentamer of dimers. If the propenoic acid held two furyl substituents, the dimers of both stereoisomers, due to steric congestion, lost the possibility of intermolecular hydrogen bonding.

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