Hydrogen bonding interactions in a-substituted cinnamic acid ester derivatives studied by FT–IR spectroscopy and calculations

Kiss T., János and Felfoldi, K. and Körtvélyesi, Tamás and Pálinkó, István (2000) Hydrogen bonding interactions in a-substituted cinnamic acid ester derivatives studied by FT–IR spectroscopy and calculations. VIBRATIONAL SPECTROSCOPY, 22 (1-2). pp. 63-73. ISSN 0924-2031

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Abstract

Intermolecular hydrogen bonding interactions in stereoisomeric cc-substituted cinnamic acid methyl esters (methyl 2,3-diphenylpropenoate, methyl 2-phenyl-3-(2'-methoxyphenyl)-propenoate, methyl 2-(2'-methoxyphenyl)-3-phenylpropenoate and methyl-2,3-bis(2'-methoxyphenyl)-propenoate) were studied by FT-IR spectroscopy and model calculations at the semi-empirical quantum chemical level of theory. Intermolecular hydrogen bonds of C-H...O types were found to be general in the solid stare, but rare in solution. In this hydrogen bond the carbon may be part of either aromatic ring or the olefinic bond. The hydrogen bond acceptor may be the carbonyl oxygen or the oxygen in the methoxy substituent. Modeling helped in determining probable hydrogen bonding sites and their positions and provided with approximate geometric parameters (bond lengths and angles). Pointing out differences between the stereoisomers was also possible.

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