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Competing tautomeric transformations and the structure of 1-(alkyl,aryl)amino-4-hydroxyanthraquinones

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Abstract

Keto-enol and amine-imine tautomerism and equilibria with trans-conformers are characteristic of 1-(alkyl,aryl)amino-4-hydroxy-9,10-anthraquinones. Amino forms possess 1,10- and 1,4-, but not 9,10-quinoid structure. Various tautomeric and conformeric transformations are in competition. The outcome of this competition may be studied by the correlation analysis of electron absorption spectra but it would be possible to understand the causes of changes in the direction of the competing transformation only in the case when each action on the substance would be accompanied with establishing the corresponding alterations in its tautomeric composition.

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Authors and Affiliations

  1. Russian University of Peoples’ Friendship, Moscow, 117198, 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 English Text © V.Ya. Fain, B.E. Zaitsev, M.A. Ryabov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 714–718.

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Fain, V.Y., Zaitsev, B.E. & Ryabov, M.A. Competing tautomeric transformations and the structure of 1-(alkyl,aryl)amino-4-hydroxyanthraquinones. Russ J Org Chem 49, 696–701 (2013). https://doi.org/10.1134/S1070428013050102

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  • DOI: https://doi.org/10.1134/S1070428013050102

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