Abstract
Molecular modeling methods were employed to investigate the potential energy surface in the valence isomerization of bis(5-thioxopenta-1,3-dien-1-yl) sulfide initiated by generation of thiirane and thiophene biradical structures in the lowest triplet state. The channel of the cascade formation of condensed systems containing the thiirane and polycyclobutane fragments was analyzed.
Similar content being viewed by others
References
Block, E. and Corey, E.J., J. Org. Chem., 1969, vol. 34, no. 4, p. 896.
Ohno, A., Intern. J. Sulfur Chem. (B), 1971, no. 6(2), p. 183.
Ohno, A., Ohnishi, Y., Tsuchihashi, G., and Fukugama, H., J. Am. Chem. Soc., 1968, vol. 90, no. 25, p. 7038.
Ohno, A., Ohnishi, Y., and Tsuchihashi, G., Tetrahedron Lett., 1969, no. 3, p. 161.
Mayo, P. and Shizuka, H., Mol. Photochem., 1973, no. 5(3), p. 339.
Mayo, P. and Shizuka, H., J. Am. Chem. Soc., 1973, vol. 95, no. 12, p. 3942.
Shagun, V.A., Smirnov, V.I., and Timokhina, L.V., Russ. J. Gen. Chem., 2007, vol. 77, no. 11, p. 1904.
Shagun, V.A., Smirnov, V.I., and Timokhina, L.V., Russ. J. Gen. Chem., 2008, vol. 78, no. 2, p. 295.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648; Lee, C., Yang, W., and Parr, R.G., Phys. Rev. (B), 1988, vol. 37, p. 785; Miehlich, B., Savin, A., Stoll, H., and Preuss, H., Chem. Phys. Lett., 1989, vol. 157, no. 3, p. 2000.
Scott, A.P. and Radom, L., J. Phys. Chem., 1996, vol. 100, no. 41, p. 16502.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.R., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B.G., Chen, W., Wong, M.W., Andres, J.L., Head-Gordon, M., Replogle, E.S., and Pople, J.A., Gaussian 98, Rev. A.6, Pittsburgh: Gaussian, 1998.
Shagun, V.A., Timokhina, L.V., and Panova, G.M., Russ. Chem. Bull., 1999, vol. 48, no. 12, p. 2229.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.A. Shagun, V.I. Smirnov, L.V. Timokhina, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 5, pp. 800–807.
Rights and permissions
About this article
Cite this article
Shagun, V.A., Smirnov, V.I. & Timokhina, L.V. Quantum chemical study of valence isomerization of bis(5-thioxopenta-1,3-dien-1-yl) sulfide in the ground and excited states. Russ J Gen Chem 79, 972–979 (2009). https://doi.org/10.1134/S1070363209050181
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363209050181