Enclathration by a xanthenol host via solid–solid reactions: structures and kinetics

Abstract

The host compound 9-(4-methoxyphenyl)-9H-xanthen-9-ol (H) forms inclusion compounds with the solid guests 1-naphthylamine, 8-hydroxyquinoline, triethylenediamine and acridine. All four structures were successfully solved in the triclinic spacegroup P 1. Similar packing motifs arise for the 1-naphthylamine and the 8-hydroxyquinoline inclusion compounds where the main interaction is of the form (host)-OHÁ Á ÁO-(host). Both the triethylenediamine and the acridine guests hydrogen bond to the host molecule. The thermal stabilities and kinetics of the solid-solid reactions were determined.

9-Methoxy-9-(2-methoxyphenyl)-9H-xanthene

“…For the synthesis of the parent xanthenol compound 9-(2methoxyphenyl)-9H-xanthen-9-ol, see: Dilthey et al (1939). For related inclusion chemistry of 9-(2-methoxyphenyl)-9Hxanthen-9-ol, see: Jacobs et al (2005Jacobs et al ( , 2007Jacobs et al ( , 2009. For related structures, see: Das et al (2007).…”

“…Xanthenol compounds have been used extensively in host-guest chemistry as versatile hosts for the inclusion of small organic guests (Jacobs et al, 2005), solvent free reactions (Jacobs et al, 2009) and guest exchange experiments (Jacobs et al, 2007). This class of compounds conforms to Weber's rules (Weber, 1991) for efficient hosts in that they are bulky and contain functionalities that can participate in hydrogen bonding.…”