The affinities of 20 hydrocarbons for the cavity formed by the inner wall of cucurbit[8]uril and a tolyl unit linked to an auxiliary guest were measured in aqueous solution. Cucurbit[8]uril and the auxiliary guest, a substituted ruthenium tris(2,2'-bipyridyl) complex bearing a trifluoromethyl F NMR probe, displayed perfect selectivity toward cyclic hydrocarbons, and cis- and trans-decalin, in particular. Unlike π-π interactions, CH-π interactions, as well as differences in hydrocarbon solvation, contribute significantly to the recognition process.
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