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Anthraquinones tautomerism: VII. Hydroxy-substituted anthraquinones

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Abstract

Tautomerism of β-mono-, β,β′-dihydroxyanthraquinones, and their anions was studied for the first time by quantum-chemical and correlation methods. 2-Hydroxyanthraquinone exists exclusively in 9,10-quinoid form, and its ionization involves a tautomeric transformation into 10-oxido-2,9-anthraquinone. β,β′-Dihydroxyanthraquinones can exist as the corresponding 9,10-, 2,9-, 2,6-, and 2,3-quinoid tautomers, and the most characteristic forms of their anions are 2,9-quinoid structures. The considerable difference in the known spectra of the same compound is due to the shifts of the tautomeric equilibria.

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Authors and Affiliations

  1. Russian University of Peoples Friendship, Moscow, 127349, Russia

    V. Ya. Fain, B. E. Zaitsev & M. A. Ryabov

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  1. V. Ya. Fain
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  2. B. E. Zaitsev
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  3. M. A. Ryabov
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Correspondence to V. Ya. Fain.

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Original Russian Text © V.Ya. Fain, B.E. Zaitsev, M.A. Ryabov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 10, pp. 1469–1473.

For Communication VI, see [1].

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Fain, V.Y., Zaitsev, B.E. & Ryabov, M.A. Anthraquinones tautomerism: VII. Hydroxy-substituted anthraquinones. Russ J Org Chem 43, 1460–1465 (2007). https://doi.org/10.1134/S1070428007100089

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