Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

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

doi:10.1021/acs.cgd.9b00369

Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

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

University of Cape Town

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	3962-3968
Number of pages	7
Journal	Crystal Growth and Design
Volume	19
Issue number	7
DOIs	https://doi.org/10.1021/acs.cgd.9b00369
Publication status	Published - 17 May 2019
Externally published	Yes

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title = "Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid",

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).",

author = "\{Bouanga Boudiombo\}, \{Jacky S.\} and Hong Su and Neil Ravenscroft and Bourne, \{Susan A.\} and Nassimbeni, \{Luigi R.\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = may,

day = "17",

doi = "10.1021/acs.cgd.9b00369",

language = "English",

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T1 - Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

AU - Bouanga Boudiombo, Jacky S.

AU - Su, Hong

AU - Ravenscroft, Neil

AU - Bourne, Susan A.

AU - Nassimbeni, Luigi R.

PY - 2019/5/17

Y1 - 2019/5/17

N2 - 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).

AB - 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).

UR - https://www.scopus.com/pages/publications/85073652665

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DO - 10.1021/acs.cgd.9b00369

M3 - Article

AN - SCOPUS:85073652665

SN - 1528-7483

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JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 7

ER -

Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

Abstract

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