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IBX Oxidation of Benzenedimethanols in the Presence of Cucurbit[8]uril
Author(s) -
Cong Hang,
Chen Qiuju,
Geng Qingxia,
Tao Zhu,
Yamato Takehiko
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400886
Subject(s) - chemistry , isothermal titration calorimetry , supramolecular chemistry , catalysis , aqueous solution , substrate (aquarium) , titration , cucurbituril , isothermal process , catalytic oxidation , combinatorial chemistry , organic chemistry , medicinal chemistry , molecule , oceanography , physics , thermodynamics , geology
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.