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A Quantum-Chemical Study of Prototropic Tautomerism in 1-Hydroxy-9,10-anthraquinones

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Abstract

The effect of substituents R on the tautomerism and electronic absorption spectra of 1-hydroxy-x-R-9,10-anthraquinones and 9-hydroxy-x-R-1,10-anthraquinones was studied by quantum-chemical and correlation methods. The former compounds (x ≠ 2) are more sensitive to substituent effects than the latter compounds. Examination of the fine structure of long-wave absorption showed that the experimental spectra of 1-hydroxy-x-R-9,10-anthraquinones contain no bands assignable to ana-quinoid forms.

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Fain, V.Y., Zaitsev, B.E. & Ryabov, M.A. A Quantum-Chemical Study of Prototropic Tautomerism in 1-Hydroxy-9,10-anthraquinones. Russian Journal of General Chemistry 73, 621–626 (2003). https://doi.org/10.1023/A:1025609107777

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