Possible Oxidative Polymerization Mechanism of 5,6-Dihydroxyindole from ab Initio Calculations

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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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