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

    23 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

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    Dimers
    polymerization
    Polymerization
    dimers
    trimers
    Coulomb interactions
    oligomers
    Oligomers
    Density functional theory
    electron transfer
    reactivity
    monomers
    Monomers
    electrostatics
    density functional theory
    5,6-dihydroxyindole
    Electrons
    predictions
    interactions

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry

    Cite this

    Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations. / Okuda, Hidekazu; Wakamatsu, Kazumasa; Ito, Shosuke; Sota, Takayuki.

    In: Journal of Physical Chemistry A, Vol. 112, No. 44, 06.11.2008, p. 11213-11222.

    Research output: Contribution to journalArticle

    Okuda, Hidekazu ; Wakamatsu, Kazumasa ; Ito, Shosuke ; Sota, Takayuki. / Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations. In: Journal of Physical Chemistry A. 2008 ; Vol. 112, No. 44. pp. 11213-11222.
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