Inclusion of carvone enantiomers in cyclomaltoheptaose (β-cyclodextrin): thermal behaviour and H→D and D→H exchange

• Published in: Carbohydrate research Vol. 337; no. 24; pp. 2501 - 2504
• Main Authors: da Silva, Aida M.Moreira, Empis, José M.A., Teixeira-Dias, José J.C.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 29.11.2002
• Subjects: beta-Cyclodextrins; Binding Sites; Carvone enantiomers; Cyclodextrins - chemistry; Deuterium; Hydrogen; H→D/D→H exchange; Inclusion compounds; Monoterpenes; Spectrum Analysis, Raman; Stereoisomerism; Temperature; Terpenes - chemistry; Thermal dehydration; Thermal guest release; Water - chemistry; β-Cyclodextrin; β-Cyclodextrin; Thermal dehydration; H→D/D→H exchange; Carvone enantiomers; Thermal guest release; Inclusion compounds
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(02)00314-2

The inclusion compounds of carvone enantiomers in cylcomaltoheptaose (β-cyclodextrin, βCD) are studied at defined temperatures above room temperature and in relation to H→D and D→H exchanges. Loss of water molecules and release of carvone molecules from the βCD cavity are caused by increase of temperature above room temperature and are measured by the integrated intensities of the OH and CH Raman stretching bands, respectively. In turn, H→D and D→H exchanges are monitored by the integrated intensities of the OH and OD Raman stretching bands, respectively. All of these processes were followed in real time with a Raman spectrometer equipped with CCD detection. The results indicate that distinct carvone enantiomers lead to the formation of different βCD inclusion hydrates that have different water content and hydration structures. In particular, the results suggest that SCarv–βCD has a greater water content, dehydrates strongly for temperatures above room temperature, and exchanges protons faster than the RCarv–βCD complex. Graphic