TY - JOUR
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.
N1 - Publisher Copyright:
© 2019 American Chemical Society.
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 - http://www.scopus.com/inward/record.url?scp=85073652665&partnerID=8YFLogxK
U2 - 10.1021/acs.cgd.9b00369
DO - 10.1021/acs.cgd.9b00369
M3 - Article
AN - SCOPUS:85073652665
SN - 1528-7483
VL - 19
SP - 3962
EP - 3968
JO - Crystal Growth and Design
JF - Crystal Growth and Design
IS - 7
ER -