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“Orientational isomerism” is a concept necessary for deeper understanding of the selective reactivities in a host-guest system. This concept has been rarely explored in the context of supramolecular host guest chemistry. We designed a model system including four cyclohexene derivatives and a water-soluble host Octa Acid (OA), with hydrophobic inner cavity. The overall length of the guest molecules (~ 12 Å) was limited by manipulating the alkyl substituents at 1- and 4-positions on the cyclohexene ring. 1D 1H /2D COSY and NOESY NMR and photooxygenation reaction were used to understand the observations with this model system. Specific packaging or “orientational isomerism” of each guest molecule, induced by the host OA led to specific, in one case enhanced product selectivity. With this model system we show the important role of “orientational isomerism” in explaining enhanced product selectivity in a host-guest supramolecular system.