Abstract
Photosubstitution of the sulfo group for hydrogen (chlorine in chloranil) is observed under irradiation of sulfonated derivatives of hydroquinone formed upon dissolving of p-benzoquinone and p-chloranil in aqueous solutions of sodium sulfite. The quantum yield of the photochemical reaction is 0.18 ± 0.02 for p-benzoquinone. The rate constant of the thermal reaction of substitution is 5.5 × 10−4 l mol−1 s−1. The substitution reaction is sensitized by eosin upon irradiation with visible light. During the course of irradiation of sulfohydroquinones, the formation of a product with an absorption maximum at 235 nm was found. The product decays with a rate constant of 0.005 s−1.
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Kurien, K.C. and Robins, P.A., J. Chem. Soc. (B), 1970, p. 855.
Kryukov, A.I. and Krasnova, V.A., Teor. Eksp. Khim., 1972, vol. 8, no. 4, p. 478.
Levin, P.P. and Kuz’min, V.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1986, no. 11, p. 2587.
Jones, G., Haney, W.A., and Phan, X.T., J. Am. Chem. Soc., 1988, vol. 110, no. 6, p. 1922.
Jones, G., Mouli, N., Haney, W.A., and Bergmark, W.R., J. Am. Chem. Soc., 1997, vol. 119, no. 38, p. 8788.
Newcomb, M., Miranda, N., Huang, X., and Crich, D., J. Am. Chem. Soc., 2000, vol. 122, no. 25, p. 6128.
Görner, H., Photochem. Photobiol., 2003, vol. 78, no. 5, p. 440.
Görner, H. and von Sonntag, C., J. Phys. Chem. A, 2008, vol. 112, no. 41, p. 10257.
Bishop, C.A., Porter, R.F., and Tong, L.K.J., J. Am. Chem. Soc., 1963, vol. 85, no. 24, p. 3991.
LuValle, J.E., J. Am. Chem. Soc., 1952, vol. 74, no. 12, p. 2970.
Youngblood, M.P., J. Org. Chem., 1986, vol. 51, no. 11, p. 1981.
Ivanov, V.L. and Artyukhin, A.B., Khim. Vys. Energ., 1998, vol. 32, no. 5, p. 372 [High Energy Chem., 1998, vol. 32, no. 5, p. 333].
Ichino, T. and Fessenden, R.W., J. Phys. Chem. A, 2007, vol. 111, no. 13, p. 2527.
Eksperimental’nye metody khimii vysokikh energii (Experimental Methods of High Energy Chemistry) Mel’nikov, M.Ya., Ed., Moscow: Mosk. Gos. Univ., 2009.
Ivanov, V.L., Aurich, J., Eggert, L., and Kuzmin, M.G., J. Photochem. Photobiol., A, 1989, vol. 50, no. 2, p. 275.
Huie, R.E. and Neta, P., J. Phys. Chem., 1985, vol. 89, no. 18, p. 3918.
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Original Russian Text © V.L. Ivanov, S.Yu. Lyashkevich, 2011, published in Khimiya Vysokikh Energii, 2011, Vol. 45, No. 3, pp. 241–244.
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Ivanov, V.L., Lyashkevich, S.Y. Photolysis of p-benzoquinone and p-chloranil in aqueous sodium sulfite solution. High Energy Chem 45, 210–213 (2011). https://doi.org/10.1134/S0018143911030064
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DOI: https://doi.org/10.1134/S0018143911030064