Hydrogen bonded networks of methoxy-substituted alpha-phenylcinnamic acids studied by spectroscopic and computational methods

Kiss T., János and Felföldi, K. and Hannus, István and Pálinkó, István (2001) Hydrogen bonded networks of methoxy-substituted alpha-phenylcinnamic acids studied by spectroscopic and computational methods. JOURNAL OF MOLECULAR STRUCTURE, 565-66. pp. 463-468. ISSN 0022-2860

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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 alpha -phenylcinnamic acid stereoisomers was the C=O . . .H-O intermolecular hydrogen bonding between the carboxylic groups. Under 10(-3) mol/dm(3) concentration no other secondary intermolecular interaction was found. In solid state, using IR spectroscopy, FT-IR and C-13 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 C-13 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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