Diastereomeric complex of (R/S)-piperidine-3-carboxylic acid with (2R,3R)-tartaric acid: Structural, spectroscopic and computational studies

作者：Bartoszak Adamska E; Dega Szafran Z^*; Jaskolski M; Szafran M

来源：Journal of Molecular Structure, 2011, 999(1-3): 98-105.

DOI：10.1016/j.molstruc.2011.05.042

• Piperidine-3-carboxylic acid
• Tartaric acid
• Hydrogen bonds
• X-ray diffraction
• FTIR and NMR spectroscopy
• DFT calculations

2:2 Complex of (R) and (S)-piperidine-3-carboxylic acids (P3C) with (2R,3R)-tartaric acid (TA). 1. has been characterized by single-crystal X-ray analysis, FTIR and NMR spectroscopies, and by DFT calculations. The crystals of 1 are monoclinic, space group P2(1). The crystal structure is formed by two distinct P3CH(+) .TA(-) components, A and B, linked by an O-H center dot center dot center dot O hydrogen bond of 2.603(2) angstrom. The A and B components differ in the absolute configuration of the C(3) atom of P3CH(+); (S) in A and (R) in B. The piperidinium-3-carboxylic acid and (2R,3R)-semi-tartrate anion moieties of the components A and B are linked by O-H center dot center dot center dot O hydrogen bonds of 2.517(1) and 2.535(1) angstrom, respectively. In A and B the piperidinium rings adopt the chair conformation with the carboxyl group in the equatorial position. The structures of the monomers of P3CH(+).TA(-), 3A and 3B, as well as of a dimer 2, have been optimized by the B3LYP/6-31G(d,p) approach. The chemical shift assignments were based on two-dimensional H-1-H-1 and H-1-C-13 experiments.

• 出版日期2011-7-27