Structure and Substituent Effects on Retention and Chiral Resolution of Ketones and Alcohols on Microcrystalline Cellulose Triacetate Plates
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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.
KeywordsThin layer chromatography Chiral separations Mechanism of chiral recognition Microcrystalline cellulose triacetate Racemic ketones and alcohols
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.
- 1.Thin layer chromatography in chiral separations and analysis. Chromatographic Science Series. 2007 Volume 98. In: Kowalska T, Sherma J (eds) CRC Press, Taylor & Francis GroupGoogle Scholar
- 2.Faupel M (1987) In: Proceedings of 4th international symposium on instrumental HPTLC, Selvino, Italy, pp147Google Scholar
- 3.Gunther K, Möller K (1996) Enantiomer separations. In: Sherma J, Fried B (eds) Handbook of thin-layer chromatography. Marcel Dekker, New York, pp 621–686Google Scholar
- 5.Lepri L, Coas V, Desideri PG, Zocchi A (1994) J Planar Chromatogr–Mod TLC 7:376–381Google Scholar
- 6.Lepri L (1995) J Planar Chromatogr–Mod TLC 8:467–469Google Scholar
- 7.Lepri L, Del Bubba M, Masi F (1997) J Planar Chromatogr–Mod TLC 10:108–113Google Scholar
- 9.Lepri L, Cincinelli A, Del Bubba M (1999) J Planar Chromatogr–Mod TLC 12:298–301Google Scholar
- 10.Lepri L, Del Bubba M, Cincinelli A, Boddi L (2000) J Planar Chromatogr–Mod TLC 13:384–387Google Scholar
- 13.Shibata T, Okamoto I, Ishin K (1986) Chromatographic optical resolution on polysaccharides and their derivatives. In: Hara S, Cazes J (eds) Optical resolution by liquid chromatography. Marcel Dekker, New York, pp 313–340Google Scholar
- 15.Lepri L, Del Bubba M, Cincinelli A, Boddi L (2001) J Planar Chromatogr–Mod TLC 14:134–137Google Scholar