Inclusion by a Xanthenol Host: Relating Structure to the Kinetics of Desolvation and Guest Exchange

Abstract

The inclusion compounds of the host 9-(4-methoxyphenyl)-9H-xanthen-9-ol, C23H16O2, with the guests cyclohexane (CHEX), 1,4-dioxane (DIOX), and N,N-dimethylformamide (DMF) have been investigated. Their crystal structures have been determined and correlated with their thermal behavior. Both dioxane and cyclohexane guests gave structures that were isostructural with respect to the host and displayed (Host)OH···O(Host) hydrogen bonding. The guests were found on centers of inversion. For the DMF structure, we observed a different packing arrangement with both the host and the guest molecules in general positions, and for the first time, this host displayed (Host)−OH···(Guest) hydrogen bonding. Kinetics of desolvation for the 1,4-dioxane and N,N-dimethylformamide compounds were studied. Guest-exchange reactions were also performed.