Issue 4, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

The oxidation of 6-hydroxydopamine in aqueous solution. Part 1. The formation of three metastable quinones at low pH †

Guy N. L. Jameson,‡*a   Andrei B. Kudryavtsev§a  and  Wolfgang Linerta  

* Corresponding authors

a Institute of Inorganic Chemistry, Technical University of Vienna, Getreidemarkt 9/153, Vienna, Austria
E-mail: gjameson@physics.emory.edu; , wlinert@mail.zserv.tuwien.ac.at

Abstract

1H and 13C NMR investigations have been carried out in order to elucidate the products of oxidation of 6-hydroxydopamine [5-(2-aminoethyl)benzene-1,2,4-triol, protonated form H3LH+]. Stopped-flow, NMR kinetic experiments, and quantum mechanical calculations were employed as additional aids to the interpretation of the results. Evidence is provided that, at low pH, three quinones are produced that are in metastable equilibrium, namely the p- ( pQ), o- (oQ), and triketo-quinones (tQ). Results obtained with sodium periodate and iron(III) are compared and discussed. At higher pHs (>2.5) the quinones reach rapid equilibrium because they start to deprotonate, all giving rise to the same species (Q−), which is the only species detectable above a pH of about 6 and which is stable over a large pH range.

Graphical abstract: The oxidation of 6-hydroxydopamine in aqueous solution. Part 1. The formation of three metastable quinones at low pH [ ]

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Article information

DOI
https://doi.org/10.1039/B007912J
Article type
Paper
Submitted
02 Oct 2000
Accepted
15 Feb 2001
First published
20 Mar 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 557-562

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The oxidation of 6-hydroxydopamine in aqueous solution. Part 1. The formation of three metastable quinones at low pH

G. N. L. Jameson, A. B. Kudryavtsev and W. Linert, J. Chem. Soc., Perkin Trans. 2, 2001, 557 DOI: 10.1039/B007912J

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