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Substituent Effects on the Driving Force for Inclusion Complexation of α- and β-Cyclodextrin with Monosubstituted Benzene Derivatives

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Abstract

The association constant values, Ka, for the inclusion of α- and β-CD with monosubstituted benzene derivatives were determined by means of UV-vis and fluorescence spectroscopy. The stability of the complexes is influenced by the properties of the substituents of the guest compounds. Regression analysis was used to create a set of inclusion models with the experimental association constant ln Ka and the corresponding substituent molar refraction Rm, hydrophobic constant π and Hammett σ constant of the benzene derivatives. The ln Ka value mainly correlated with Rm for α-CD and with both Rm and π for β-CD complexes. The association constants predicted by the models are in good agreement with the experimentally determined data. This suggests that the inclusion complexation of benzene derivatives with α-CD is predominantly driven by van der Waals force and with β-CD mainly by van der Waals force and hydrophobic interactions.

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Authors and Affiliations

  1. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. China

    Qing-Xiang Guo & You-Cheng Liu

  2. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China

    Qing-Xiang Guo, Shuang-Hui Luo & You-Cheng Liu

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  1. Qing-Xiang Guo
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  2. Shuang-Hui Luo
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Guo, QX., Luo, SH. & Liu, YC. Substituent Effects on the Driving Force for Inclusion Complexation of α- and β-Cyclodextrin with Monosubstituted Benzene Derivatives. Journal of Inclusion Phenomena 30, 173–182 (1998). https://doi.org/10.1023/A:1007985107256

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