Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations |
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Authors: | Okuda Hidekazu Wakamatsu Kazumasa Ito Shosuke Sota Takayuki |
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Institution: | Integrative Bioscience and Biomedical Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan. h.okuda@asagi.waseda.jp |
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Abstract: | The reactivity of 5,6-dihydroxyindole and its major dimers has been studied with the use of a recently proposed general-purpose reactive indicator (Anderson et al. J. Chem. Theory Comput. 2007, 3, 358-374) from ab initio density-functional theory calculations. Theoretical prediction has reasonably explained previously isolated oligomers up to tetramers. The oxidative polymerization is governed by the electron-transfer-controlled reaction. The electrostatic interaction plays a regioselective role in the reactant complex and/or intermediates. A monomer-dimer coupling is able to form trimers, while a part of it is prevented by the exchange repulsion, i.e., steric hindrance. Therefore, a dimer-dimer coupling is also able to form tetramers. |
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