engleski

Experiments and Models in Enantiorecognition by Chiral Pirkle-Type Stationary Phases Containing Aromatic pi-Acid Branching Units

Overview of the projects in the authors laboratory aimed to development of novel chiral stationary phases (CSPs) is presented. Emphasis is given on the origin of the concept to use of 2, 4, 5, 6-tetrachloro-1, 3-dicyanobenzene (TCDCB) and 4-chloro-3, 5-dinitrobenzoic acid (CDNB) as the branching units in the Pirkle-type (brush-type) CSPs. Preparations of nearly hundred novel CSPs, requiring synthesis of nearly three hundred of new compounds as intermediates or model structures, are described. Specific recognition properties and enantioselection efficacy of the individual CSPs is demonstrated for various sets of the test racemates (TR). Correlation between structure and conformational properties of chiral selectors and racemic analytes is discussed. Specific properties of some CSPs, as their capacity enhancement by introducing the tweezer unit in chiral selector, and catalysis of enantiomerization proces of configurationally unstable analyte are discussed. Mechanism of enantiorecognition of some TRs by structuraly related CSPs is suggested.

chirality; liquid chromatography; enantiorecognition

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