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 α-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)O 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.
ASJC Scopus subject areas
- Condensed Matter Physics
- Physical and Theoretical Chemistry