Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

Jacky S. Bouanga Boudiombo, Hong Su, Neil Ravenscroft, Susan A. Bourne, Luigi R. Nassimbeni

Research output: Contribution to journalArticlepeer-review

Abstract

Deoxycholic acid (DCA) includes all the isomers of methylcyclohexanones (MCH). Competition experiments showed that the preference is 2MCH > 3MCH > 4MCH confirmed by crystal structure analysis, NMR, and thermal analysis. DCA resolves 2MCH, enclathrating the S-conformer, whereas 3MCH remains unresolved. However, in competition experiments of rac-2MCH/rac-3MCH, both guests are resolved yielding S-conformers, suggesting that 2MCH has a templating effect on the final structures. The activation energies of desolvation of the clathrates with 2MCH and 3MCH are similar (∼74 kJ/mol) but significantly lower for 4MCH (∼48 kJ/mol).

Original languageEnglish
Pages (from-to)3962-3968
Number of pages7
JournalCrystal Growth and Design
Volume19
Issue number7
DOIs
Publication statusPublished - 17 May 2019
Externally publishedYes

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