Structure and Substituent Effects on Retention and Chiral Resolution of Ketones and Alcohols on Microcrystalline Cellulose Triacetate Plates

• Published in: Chromatographia Vol. 71; no. 7-8; pp. 685 - 694
• Main Authors: Lepri, Luciano, Cincinelli, Alessandra, Checchini, Leonardo, Del Bubba, Massimo
• Format: Journal Article
• Language: English
• Published: Wiesbaden Wiesbaden : Vieweg Verlag 2010; Vieweg Verlag; Springer
• Subjects: Analytical Chemistry; Chemistry; Chemistry and Materials Science; Chiral separations; Chromatographic methods and physical methods associated with chromatography; Chromatography; Exact sciences and technology; Laboratory Medicine; Mechanism of chiral recognition; Microcrystalline cellulose triacetate; Original; Other chromatographic methods; Pharmacy; Proteomics; Racemic ketones and alcohols; thin layer chromatography; Mechanism of chiral recognition; Thin layer chromatography; Chiral separations; Microcrystalline cellulose triacetate; Racemic ketones and alcohols; Microcrystalline material; Separation; Chromatographic retention; Lactam; Chiral recognition; Mechanism; Racemic; Enantiomer; Bicyclic compound; Aromatic compound; Densitometry; Secondary alcohol; Oxygen nitrogen heterocycle; Stationary phase; Lactone; Ketone; Ultraviolet detector; Optical resolution; Carboxamide; Benzamide derivatives; Property structure relationship; Cellulose acetate
• ISSN: 0009-5893; 1612-1112
• DOI: 10.1365/s10337-010-1508-y

This paper reports a number of original thin layer chromatography enantioseparations of closely related ketones and alcohols such as tetralones, indanones, and benzhydrols carried out by elution with aqueous-alcoholic mixtures at different ratios. In order to investigate the structural and substituent effects on chiral recognition of microcrystalline cellulose triacetate, the results were compared with those obtained in previous papers for analogous compounds in similar experimental conditions. Even though the inclusion model of retention of analytes on this chiral stationary phase is confirmed, different and unexpected results were obtained for compounds having very favourable characteristics for resolution.