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 language | English |
|---|---|
| Pages (from-to) | 201-208 |
| Number of pages | 8 |
| Journal | Journal of Molecular Structure |
| Volume | 615 |
| Issue number | 1-3 |
| DOIs | |
| State | Published - 26 Sep 2002 |
| Externally published | Yes |
Keywords
- Hydrogen bond
- Piperidinecarboxylic acids
- Semi-empirical calculations
- X-ray structure