Abstract
The quantum-chemical method B3LYP/6-311G(d,p) was used to calculate structural parameters of four conformers of 9,10-dihydroxyanthracene, two conformers of 9-hydroxyanthrone, and the corresponding anions, dianion, and radical anion. The energy of 9,10-dihydroxyanthracene in a gas phase is higher and in aqueous solution lower than the energy of 9-hydroxyanthrone. The dianion can exist exclusively in a polarizable medium.
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Landucci, L.L. and Ralf, J., J. Org. Chem., 1982, vol. 47, no. 18, p. 3486. DOI: 10.1021/jo00139a020.
Semenov, S.G. and Shevchenko, S.M., Zh. Org. Chem., 1983, vol. 19, no. 5, p. 1084.
Anthraquinone Pulping: A Tappi Press Anthology of Published Papers, 1977–1996, Goyal, G.C., Ed., Atlanta: Tappi, 1997.
van Dijk, E.H., Myles, D.J.T., van der Veen, M.H., and Hummelen, J.C., Org. Lett., 2006, vol. 8, no. 11, p. 2333. DOI: 10.1021/ol0606278.
Markussen, T., Schiotz, J., and Thygesen, K.S., J. Chem. Phys., 2010, vol. 132, no. 22, p. 224104–1.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., GAUSSIAN-03, Rev. B.05. Pittsburgh, PA: Gaussian, 2003.
Tomasi, J. and Persico, M., Chem. Rev., 1994, vol. 94, no. 7, p. 2027. DOI: 10.1021/cr00031a013.
Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, no. 8, p. 2999. DOI: 10.1021/cr9904009.
Shevchenko, S.M. and Semenov, S.G., Zh. Org. Chem., 1984, vol. 20, no. 4, p. 785.
Shevchenko, S.M. and Gindin, V.A., Zh. Org. Chem., 1982, vol. 18, no. 10, p. 2216.
Bredereck, K. and Sommermann, E.F., Tetrahedron Lett., 1966, vol. 7, no. 41, p. 5009. DOI: 10.1016/S0040-4039(00)90318-6.
Carlson, S.A. and Hercules, D.M., Anal. Chem., 1973, vol. 45, no. 11, p. 1794. DOI: 10.1021/ac60333a047.
Takatsuka, K., Fueno, T., and Yamaguchi, K., Theor. Chim. Acta, 1978, vol. 48, no. 3, p. 175. DOI: 10.1007/BF00549017.
Reed, A.E., Weinstock, R.B., and Weinhold, F., J. Chem. Phys., 1985, vol. 83, no. 2, p. 735. DOI: 10.1063/1.449486.
Glendening, E.D., Reed, A.E., and Weinhold, F., NBO, Ver. 3.1.
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Original Russian Text © S.G. Semenov, M.V. Makarova, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 750–754.
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Semenov, S.G., Makarova, M.V. Quantum-chemical study of tautomers of reduced forms of anthraquinone. Russ J Gen Chem 84, 843–847 (2014). https://doi.org/10.1134/S1070363214050107
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DOI: https://doi.org/10.1134/S1070363214050107