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Characterization of host–guest complexes of cucurbit[n]uril (n = 6, 7) by electrospray ionization mass spectrometry

Authors

  • Issey Osaka,

    1. Department of Applied Chemistry, Kansai University, Yamatecho, Suita 564-8680, Japan
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  • Masanobu Kondou,

    1. Department of Applied Chemistry, Kansai University, Yamatecho, Suita 564-8680, Japan
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  • Narayanan Selvapalam,

    1. National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31 Hyojadong, Pohang 790-784, Korea
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  • Shashadhar Samal,

    1. National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31 Hyojadong, Pohang 790-784, Korea
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  • Kimoon Kim,

    1. National Creative Research Initiative Center for Smart Supramolecules, and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31 Hyojadong, Pohang 790-784, Korea
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  • Mikhail V. Rekharsky,

    1. Entropy Control Project, ICORP, JST, 4-6-3 Kamishinden, Toyonaka 560-0085, Japan
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  • Yoshihisa Inoue,

    1. Entropy Control Project, ICORP, JST, 4-6-3 Kamishinden, Toyonaka 560-0085, Japan
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  • Ryuichi Arakawa

    Corresponding author
    1. Department of Applied Chemistry, Kansai University, Yamatecho, Suita 564-8680, Japan
    • Department of Applied Chemistry, Kansai University, Suita, Osaka 564-8680, Japan.
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Abstract

When an intramolecular cavity exists in a molecule, it can trap another chemical species to form a host–guest complex. We examine the formation of such an inclusion complex with cucurbit[n]uril (CBn, n = 6, 7) as the host to trap alkali metal or ammonium ions as the guest, by electrospray ionization mass spectrometry (ESI-MS). The results show that the inclusion complexes are formed between the three-dimensional cylinder of CBn hosts and the guest cations. Selectivity of the complex formation is dependent both on (1) ion–dipole interactions between the cylindrical portal of the CBn hosts and the guest cations and (2) the hydrophobic interactions at the inner cavity of CBn. Copyright © 2006 John Wiley & Sons, Ltd.

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