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Characterization of inclusion complexation of various tetraalkylammonium chlorides with cucurbit[7]uril by external high-pressure studies

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Abstract

The inclusion constants of tetraalkylammonium salts (ASs) with cucurbit[7]uril (CB[7]) were determined at high-pressures using methylene blue as a chemical indicator. CB[7] formed 1:1 inclusion complexes with ASs. We found a characteristic dependence of the alkyl chain substituents in ASs on the inclusion equilibrium, which was responsible for the formation of clathrate hydrates of the AS in bulk. Furthermore, we examined the effects of external high pressures on the CB[7] inclusion complexations of ASs having different alkyl chain lengths. Pressure dependence experiments allowed us to calculate the reaction volume (ΔV) upon inclusion; i.e., the volume change (ΔVdesolv) accompanying desolvation around the guest molecules and the volume change (ΔVrepel) caused by the water molecules repelled from the CB[7] cavity. The volumetric study for the inclusion of ASs with CB[7] showed that in the tetraheptylammonium ion, one arm (alkyl chain) was encapsulated in the CB[7] cavity, while in other ASs, two arms were located in the cavity. NMR measurements of the complexes and pressure-dependent studies provided unique information on the structures of the inclusion complexes of ASs with CB[7].

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan

    Yuki Matsumoto, Tadashi Hanaya & Yoshimi Sueishi

  2. Technical Support Division, Graduate School of Science, Osaka University, Toyonaka, Osaka, 560-0043, Japan

    Naoya Inazumi

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  1. Yuki Matsumoto
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  2. Naoya Inazumi
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  3. Tadashi Hanaya
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  4. Yoshimi Sueishi
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Correspondence to Yoshimi Sueishi.

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Matsumoto, Y., Inazumi, N., Hanaya, T. et al. Characterization of inclusion complexation of various tetraalkylammonium chlorides with cucurbit[7]uril by external high-pressure studies. J Incl Phenom Macrocycl Chem 92, 205–210 (2018). https://doi.org/10.1007/s10847-018-0832-y

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  • DOI: https://doi.org/10.1007/s10847-018-0832-y

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