Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations

Hidekazu Okuda, Kazumasa Wakamatsu, Shosuke Ito, Takayuki Sota

Research output: Contribution to journalArticle

24 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)11213-11222
Number of pages10
JournalJournal of Physical Chemistry A
Volume112
Issue number44
DOIs
Publication statusPublished - 2008 Nov 6

    Fingerprint

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this