Abstract
The transition states of the reaction of electrophilic substitution in a series of ortho-, meta-, and para-carboranes were found by calculations in the B3PW91/6-31G(d,p) and B3LYP/6-31G(d,p) approximations. The key role of catalyst was demonstrated in the reactions of halogenation and alkylation. The reaction selectivity of electrophilic alkylation by CH3Br in the presence of AlCl3 should be lower than that of the chlorination reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
King, R.B., Izv. Akad. Nauk, Ser. Khim., 1993, no. 8, p. 1353.
Zheng, Z., Jiang, W., Zinn, A.A., Knobler, C.B., and Hawthorne, M.F., Inorg. Chem., 1995, vol. 34, no. 8, p. 2095.
Zakharkin, L.I., Pisareva, I.V., and Bikkineev, R.Kh., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, no. 3, p. 641.
Zakharkin, L.I., Ol’shevskaya, V.A., Vorontsov, E.V., and Petrovskii, P.V., Izv. Akad. Nauk, Ser. Khim., 1996, no. 11, p. 2755.
Zakharkin, L.I., Ol’shevskaya, V.A., and Anikina, E.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1987, no. 4, p. 869.
Potenza, J.A., Lipscomb, W.N., Vickers, G.D., and Schroeder, H.A., J. Am. Chem. Soc., 1966, vol. 88, p. 628.
Knyazev, S.P., Gordeev, E.G., and Chernyshev, E.A., Izv. Akad. Nauk, Ser. Khim., 2006, no. 12, p. 2074.
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, J.A., Jr., 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, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., GAUSSIAN 09, Revision A.02. Gaussian, Inc., Wallingford CT, 2009.
Keith, T.A., AIMAll (Version 09.10.24, Standard), 2009 (aim.tkgristmill.com).
Bader, R.F.W., Atoms in Molecules: A Quantum Theory, Moscow: Mir, 2001.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © S.P. Knyazev, E.G. Gordeev, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 9, pp. 1466–1472.
Rights and permissions
About this article
Cite this article
Knyazev, S.P., Gordeev, E.G. Retrieval and analysis of transition states in electrophilic substitution reactions of the carborane(12) series. Russ J Gen Chem 82, 1517–1523 (2012). https://doi.org/10.1134/S1070363212090101
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363212090101