Abstract
Charge distribution and frontier orbital energies of styrene, C,N-diphenylnitrone, and their (arene)-(tricarbonyl)chromium complexes were calculated by quantum chemical methods. The difference in the HOMO and LUMO energies of the chromium complexes was found to be smaller than in the free ligands, and the reactions with (arene)(tricarbonyl)chromium complexes were characterized by higher rate and selectivity.
Similar content being viewed by others
References
Gilchrist, T.L., Heterocyclic Chemistry, Harlow, Essex, England: Longman Scientific & Technical, 1992, 2nd ed. Translated under the title Khimiya geterotsiklov, Moscow: Mir, 1996, p. 111.
Gothelf, K.V. and Jørgensen, K.A., Chem. Rev., 1998, vol. 98, p. 863; Gothelf, K.V. and Jørgensen, K.A., Chem. Commun., 2000, p. 1449; Confalone, P.N. and Huie, E.M., Org. React., 1988, vol. 36, p. 1; Nguyen, T.B., Martel, A., Dhal, R., and Dujardin, G., J. Org. Chem., 2008, vol. 73, p. 2621.
Artemov, A.N., Sazonova, E.V., Mavrina, E.A., and Zarovkina, N.Yu., Russ. Chem. Bull., Int. Ed., 2012, vol. 61, no. 11, p. 2076.
Artemov, A.N., Sazonova, E.V., and Zarovkina, N.Yu., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, no. 6, p. 1382.
Mukai, C., Kim, I.J., Cho, W.J., Kido, M., and Hanaoka, M., J. Chem. Soc., Perkin Trans. 1, 1993, p. 2495.
Mukai, C., Kim, I.J., Cho, W.J., and Hanaoka, M., Tetrahedron Lett., 1990, vol. 31, p. 6893.
Houk, K.N., Bimanand, A., Mukherjee, D., Sims, J., Chang, Y.-M., Kaufman, D.S., and Domelsmith, L.N., Heterocycles, 1977, vol. 7, p. 293.
Woodward, R.B. and Hoffman, R., J. Am. Chem. Soc., 1965, vol. 87, p. 395.
Woodward, R.B. and Hoffmann, R., The Conservation of Orbital Symmetry, New York: Academic, 1970. Translated under the title Sokhranenie orbital’noi simmetrii, Moscow: Mir, 1971, p. 16.
Huisgen, R., Grashey, R., Hawk, H., and Seidl, H., Chem. Ber., 1968, vol. 101, p. 2548.
Sustmann, R., Tetrahedron Lett., 1971, vol. 12, no. 29, p. 2717.
Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Jr., Organic Solvents: Physical Properties and Methods of Purification, New York: Intersci., 1955, 2nd ed.
Raush, M.D., Moser, G.A., Zaiko, E.S., and Lipman, A.L., J. Organomet. Chem., 1970, vol. 23, p. 185.
Heusler, K., Wieland, P., and Meystre, Ch., Organic Syntheses, Baumgarten, H. E., Ed., New York: Wiley, 1973, collect. vol. 5, p. 1124.
Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 209.
Hohenberg, P. and Kohn, W., Phys. Rev. B, 1964, vol. 136, p. 864.
Kohn, W. and Sham, L.J., Phys. Rev. A, 1965, vol. 140, p. 1133.
Becke, A.D., Phys. Rev. A, 1988, vol. 38, p. 3098.
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785.
Hay, P.J. and Wadt, W.R., J. Chem. Phys., 1985, vol. 82, p. 270.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision A.1, Wallingford CT: Gaussian, 2009.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © N.Yu. Zarovkina, E.V. Sazonova, A.N. Artemov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 1044–1048.
Rights and permissions
About this article
Cite this article
Zarovkina, N.Y., Sazonova, E.V. & Artemov, A.N. Quantum chemical simulation of 1,3-dipolar cycloaddition of nitrones to alkenes and their (η6-arene)(tricarbonyl)-chromium complexes. Russ J Org Chem 50, 1028–1032 (2014). https://doi.org/10.1134/S1070428014070161
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014070161