DICARBOXIMIDE-BASED CLATHRATE DESIGN. HOST SYNTHESIS, INCLUSION FORMATION AND X-RAY CRYSTAL STRUCTURES OF A FREE HOST AND OF INCLUSION COMPOUDS WITH 2- AND 3-METHYLCYCLOHEXANONE, 3-METHYLCYCLOPENTANONE, BUTYRONITRILE, PROPAN-1-OL and (-)-FENCHONE GUESTS

Article abstract of DOI:10.1002/poc.610080306

Crystalline host compounds consisting of a roof-shaped dicarboximide framework and pendant diarylethanol analogous subunits were synthesized and shown to form inclusion complexes with small organic molecules such as alcohols, amines, ketones or polar and apolar organic solvents.Clathrate efficiency and selectivity depend on the particular host structure.The crystal and molecular structures of a free host compound (2a) and inclusion compounds <2a*3-methylcyclohexanone (1:1). 1a*3-methylcyclopentanone (1:1), 1a*2-methylcyclohexanone (1:1), 1b*butyronitrile (1:1), 1b*propan-1-ol (2:1) and 1b*(-)-fenchone (1:1)> were determined by x-ray diffraction analysis.In all the structures, the hydroxyl group is involved in intramolecular hydrogen bonds and the host and guest molecules are held by lattice forces only.The channels and cavities left in the host matrix are large enough to allow disorder or high thermal displacement parameters of the guest molecules.The local packing coeffecients for all guests are 0.42 on average.