Volume 33, Issue 5 pp. 545-549
Full Paper

IBX Oxidation of Benzenedimethanols in the Presence of Cucurbit[8]uril

Hang Cong

Corresponding Author

Hang Cong

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan

Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan

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Qiuju Chen

Qiuju Chen

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

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Qingxia Geng

Qingxia Geng

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

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Zhu Tao

Zhu Tao

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

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Takehiko Yamato

Corresponding Author

Takehiko Yamato

Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan

Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China

Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan

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First published: 30 March 2015
Citations: 8

Abstract

The cucurbit[8]uril (Q[8]) mediated oxidation of benzenedimethanols with o-iodoxybenzoic acid (IBX) in aqueous solution has been investigated, and the results reveal the supramolecular catalysis depends on the electronic and geometric structure of substrate. In the cases of o-benzenedimethanol (1a) and m-benzenedimethanol (1b), the IBX oxidation could be obviously enhanced by the addition of Q[8] at different extent. There is no observation of the catalytic activity of Q[8] when p-benzenedimethanol (1c) is subjected to the IBX oxidation. The addition amount of Q[8] is discussed herein, and the addition of more than 10% mol catalyst cannot improve the oxidation much more. The investigation of host-guest interactions by isothermal titration calorimetry implies the supramolecular catalysis is related to the formation of complexes between benzenedimethanols and cucurbit[8]uril.

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