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Issue 9, 2017
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Endo/exo binding of alkyl and aryl diammonium ions by cyclopentanocucurbit[6]uril

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Abstract

The binding interactions of CyP6Q[6] with a series of alkyl diammonium (+H3N(CH2)nNH3+, n = 2, 4, 6, 8, 10, 12) and aryl diammonium (p-phenylenediammonium and p-xylenediammonium) ions both in aqueous solution and in the solid state have been studied by 1H NMR spectroscopy, X-ray crystallography, and isothermal titration calorimetry (ITC) techniques. 1H NMR data indicate that all guests exhibit endo binding with CyP6Q[6] except for the ethanediammonium ion, which bound exo to CyP6Q[6]. p-Xylenediammonium ions show mixed behavior (exo and endo binding with CyP6Q[6]). X-ray crystallography clearly displays the extended and contorted conformations of the guests when bound within CyP6Q[6]. The ITC study points out that the CyP6Q[6] complex formations with all guests are mainly driven by enthalpy, which arises from the ion–dipole interactions and the hydrophobic effects.

Graphical abstract: Endo/exo binding of alkyl and aryl diammonium ions by cyclopentanocucurbit[6]uril

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Publication details

The article was received on 13 May 2017, accepted on 10 Jun 2017 and first published on 12 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00376E
Citation: Org. Chem. Front., 2017,4, 1799-1805
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    Endo/exo binding of alkyl and aryl diammonium ions by cyclopentanocucurbit[6]uril

    Y. Qu, R. Lin, Y. Zhang, K. Zhou, Q. Zhou, Q. Zhu, Z. Tao, P. Ma, J. Liu and G. Wei, Org. Chem. Front., 2017, 4, 1799
    DOI: 10.1039/C7QO00376E

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