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The formations of host–guest complexes between cucurbituril and a series of N-substituted N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution have been investigated using 1H NMR spectroscopy and electrospray ionization mass spectrometry. Dications comprising the N-methylheterocyclic head groups, bridged by a decamethylene chain, form sequential 1:1 (pseudorotaxanes) and 2:1 host–guest complexes with cucurbituril. The cucurbituril initially resides over the decamethylene chain, however with further additions of the host molecule a translocation of the hosts to the cationic N-heterocyclic head groups occurs. The order of the magnitude of the cucurbituril host–guest stability constants, determined by competitive 1H NMR binding experiments, follows the trend in the hydrophobicity of the quaternary ammonium cations.
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Organic & Biomolecular Chemistry
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