Abstract
Measurements by infrared (FT-IR) spectroscopy revealed that in solutions of low concentration the major structure forming force (short-range ordering) between methoxy-substituted α-phenylcinnamic acid stereoisomers was the CO⋯H–O intermolecular hydrogen bonding between the carboxylic groups. Under 10−3mol/dm3 concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and 13C NMR spectroscopies, it was possible to detect (aromatic)C–H⋯O hydrogen bonds, which were thought to be responsible for long-range ordering. Through the comparison of 13C chemical shifts in the liquid phase and the solid state (olefinic)C–H⋯O interactions were sought for. Such interactions could not be found for the methoxy derivatives. Molecular modeling provided structural semiquantitative information for the hydrogen bonds detected by IR spectroscopy and gave additional proof for the existence of (aromatic)C–H⋯O and the non-existence of (olefinic)C–H⋯O hydrogen bonds.
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