A. J. Mora, G. Delgado, B. Ramirez
Sep 26, 2002
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Journal
Journal of Molecular Structure
Abstract
AbstractIn this work we have investigated the hydrogen bond scheme of 4-piperidinecarboxylic (isonipecotic) acid by means of X-raydiffraction, NMR spectroscopy and semi-empirical calculations. The 4-piperidinecarboxylic acid displays a three-dimensionalassembly of hydrogen bonds. Hence, infinite chains of amino acid molecules linked by amino–carboxylate intermolecularhydrogen bonds run parallel to the b and c axes; additionally, chains of amino acid molecules intercalated with water moleculesheld together by water–carboxylate hydrogen bonds run parallel to the a axis. The theoretical calculations show largecooperative effects for the first of the amino acid chains mentioned above, which is manifested as shortening on the amino–carboxylate hydrogen bond distances and decreasing of the hydrogen bond enthalpies per monomer of the hydrogen bondedclusters, with increment of monomers in the chain. q 2002 Elsevier Science B.V. All rights reserved. Keywords: Piperidinecarboxylic acids; Hydrogen bond; X-ray structure; Semi-empirical calculations