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

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Abstract

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.

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Acknowledgments

The authors are grateful to Mrs. Susan Mary Cadby, who revised the language of the manuscript. The authors also wish to thank Mr. Pierluigi Cresci for his technical support.

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Authors and Affiliations

  1. Department of Chemistry, University of Florence, Via della Lastruccia 3, 50019, Sesto Fiorentino, Florence, Italy

    Luciano Lepri, Alessandra Cincinelli, Leonardo Checchini & Massimo Del Bubba

Authors
  1. Luciano Lepri
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  2. Alessandra Cincinelli
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  3. Leonardo Checchini
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  4. Massimo Del Bubba
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Correspondence to Massimo Del Bubba.

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Lepri, L., Cincinelli, A., Checchini, L. et al. Structure and Substituent Effects on Retention and Chiral Resolution of Ketones and Alcohols on Microcrystalline Cellulose Triacetate Plates. Chroma 71, 685–694 (2010). https://doi.org/10.1365/s10337-010-1508-y

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  • DOI: https://doi.org/10.1365/s10337-010-1508-y

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