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.
Similar content being viewed by others
REFERENCES
Fain, V.Ya., 9,10-Antrakhinony i ikh primenenie (9,10-Anthraquinones and Their Applications), Moscow: Tsentr Fotokhimii Ross. Akad. Nauk, 1999.
Minkin, V.I., Olekhnovich, L.P., and Zhdanov, Y.A., Molecular Design of Tautomeric Compounds Dordrecht: Reidel, 1988.
Gorelik, M.V., Khimiya antrakhinonov i ikh proizvodnykh (Chemistry of Anthraquinones and Their Derivatives), Moscow: Khimiya, 1983.
Gorelik, M.V., Sib. Khim. Zh. 1992, issue 4, p. 5.
Nagaoka, S. and Negoshima, U., Chem. Phys. 1996, vol. 206, no. 3, p. 353.
Marzocchi, M.P., Mantini, A.R., Cazu, M., and Smulevich, G., J. Chem. Phys. 1998, vol. 108, no. 2, p. 534.
Smith, T.P., Zaklika, K.A., Thakur, K., Walker, G.C., Tominaga, K., and Barbara, P.F., J. Phys. Chem. 1991, vol. 95, no. 25, p. 10465.
Gritsan, N.P., Klimenko, L.S., Leonenko, Z.V., Mainagashev, I.Y., Manatyuk, V.I., and Vetchinov, V.P., Tetrahedron 1995, vol. 51, no. 10, p. 3061.
Sverdlova, O.V., Elektronnye spektry v organicheskoi khimii (Electronic Spectra in Organic Chemistry), Leningrad: Khimiya, 1985, p. 193.
Dewar, M.J.S., The Molecular Orbital Theory of Organic Chemistry New York: McGraw-Hill, 1969.
Nishimoto, K. and Forster, L.S., Theor. Chim. Acta 1966, vol. 4, no. 2, p. 155.
Kogo, Y., Kikuchi, H., Matsuoka, M., and Kitao, T., J. Soc. Dyers Colour. 1980, vol. 96, no. 9, p. 475.
Fain, V.Ya., Reakts. Sposobn. Org. Soedin. 1973, vol. 10, no. 4, p. 945.
Fain, V.Ya., Available from ONIITEKhim, Cherkassy, 1989, no. 942-KhP.
Fain, V.Ya., Available from ONIITEKhim, Cherkassy, 1990, no. 163-KhP.
Fain, V.Ya., Kliot, L.Ya., Ivanov, Yu.V., Skotnikova, T.M., and Zaitsev, B.E., Reakts. Sposobn. Org. Soedin. 1985, vol. 22, no. 3, p. 309.
Fain, V.Ya., Tablitsy elektronnykh spektrov pogloshcheniya antrakhinona i ego proizvodnykh (Tables of Electronic Absorption Spectra of Anthraquinone and Its Derivatives), Leningrad: Khimiya, 1970.
Kubanov, V.A., Zhukov, V.P., and Litinskii, A.O., Poluempiricheskie metody molekulyarnykh orbitalei v kvantovoi khimii (Semiempirical Molecular Orbital Methods in Quantum Chemistry), Moscow: Nauka, 1976.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
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
Issue Date:
DOI: https://doi.org/10.1023/A:1025609107777