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Tautomerism of anthraquinones: VIII. Tautomerism and conformations of 1,4-diamino-9,10-anthraquinone

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Abstract

The compound widely known as 1,4-diamino-9,10-anthraquinone is in fact an equilibrium mixture of 4,9-diamino-1,10-anthraquinone and tautomeric imino forms, 10-amino-9-hydroxy-1,4-anthraquinone 1-imine and its conformer, and 4-amino-1-hydroxy-9,10-anthraquinone 9-imine or 4,9-dihydroxy-1,10-anthraquinone diimine. Amino-imino tautomerism and rotational isomerism are responsible for fine structure of the πl,π*-absorption of the title compound.

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Authors and Affiliations

  1. Russian University of Peoples’ Friendship, ul. Miklukho-Maklaya 6, 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 Russian Text © V.Ya. Fain, B.E. Zaitsev, M.A. Ryabov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 386–394.

For communication VII, see [1].

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Fain, V.Y., Zaitsev, B.E. & Ryabov, M.A. Tautomerism of anthraquinones: VIII. Tautomerism and conformations of 1,4-diamino-9,10-anthraquinone. Russ J Org Chem 45, 374–382 (2009). https://doi.org/10.1134/S1070428009030051

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