The role of H-bonding in the structure of the 4-piperidinecarboxylic acid monohydrate

Asiloé J. Mora, Gerzon Delgado, Belkis M. Ramírez, Luis Rincón, Rafael Almeida, Javier Cuervo, Alí Bahsas

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

In this work we have investigated the hydrogen bond scheme of 4-piperidinecarboxylic (isonipecotic) acid by means of X-ray diffraction, NMR spectroscopy and semi-empirical calculations. The 4-piperidinecarboxylic acid displays a three-dimensional assembly of hydrogen bonds. Hence, infinite chains of amino acid molecules linked by amino-carboxylate intermolecular hydrogen bonds run parallel to the b and c axes; additionally, chains of amino acid molecules intercalated with water molecules held together by water-carboxylate hydrogen bonds run parallel to the a axis. The theoretical calculations show large cooperative 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 bonded clusters, with increment of monomers in the chain.

Original languageEnglish
Pages (from-to)201-208
Number of pages8
JournalJournal of Molecular Structure
Volume615
Issue number1-3
DOIs
StatePublished - 26 Sep 2002
Externally publishedYes

Keywords

  • Hydrogen bond
  • Piperidinecarboxylic acids
  • Semi-empirical calculations
  • X-ray structure

Fingerprint

Dive into the research topics of 'The role of H-bonding in the structure of the 4-piperidinecarboxylic acid monohydrate'. Together they form a unique fingerprint.

Cite this