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NMR and HPLC Study of Chiral Recognition Mechanism

Enantioseparations by liquid chromatography (LC) have considerably advanced during the past decade not only for determining enantiomeric purity but also for preparative isolating the pure enantiomers. The preparation of a chiral stationary phase (CSP) capable of effective chiral recognition is the key in this separation technique. NMR can be the most useful spectroscopic tool in the search for chiral recognition properties of the selector. In both chiral chromatography and chiral NMR the formation of diastereomeric complexes is essential for the observed enantiodiscrimination. An obvious advantage of studying chiral selectors in solution is that there are no interfering contributions of non-selective interactions from the support. Recently, CSPs based on L-alanine and 4-chloro-3, 5-dinitrobenzoic acid were reported by our group and used for the liquid chromatography resolution of several racemic dihydropyrimidonic compounds (DHPM), known biologically active substances. Another CSPs, based on amino acid and 1, 3-dicyanotetrachlorobenzene, exhibit the good separations of binaphthol enantiomers. Herein, we report a NMR studies of the soluble chiral selectors analogous to above-mentioned CSPs against a DHPM compounds or binaphthol, respectively.

NMR; HPLC; chiral recognition

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