Abstract
The potential functions of internal rotation around the Csp2-Se bond in selenoanisole were ob- tained by quantum-chemical calculations in the approximations HF/3-21G(d), HF/6-31G(d), MP2(f)/6-31G(d), and B3LYP/6-31G(d). The calculations were performed in the range of variation of the torsion angle φ (between the planes of the benzene ring and Csp2-Se-Csp3 bonds) from 0° to 90° with 15° step. The energy minimum is in the region of the orthogonal conformation (φ 90°), and the energy maximum, in the region of the planar form (φ 0°). The rotation barriers (kJ mol- 1) are as follows: HF/3-21G(d), 9.20; HF/6-31G(d), 13.13; MP2(f)/6-31G(d), 10.25; and B3LYP/6-31G(d), 6.41. The geometric parameters, Koopmans ionization potentials, and dipole moments are given. The energies, degrees of hybridization, populations of the lone electron pairs of Se, energies of their interaction with the antibonding π* orbitals of the benzene ring, and electron density distributions were determined in terms of the natural bond orbital approach.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Zaripov, N.M., Golubinskii, A.V., Chmutova, G.A., and Vilkov, L.V., Zh. Strukt. Khim., 1978, vol. 19, no. 5, p. 894.
Vereshchagin, A.N., Chmutova, G.A., Cheryukanova, G.Ya., and Kataev, E.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1973, no. 6, p. 1244.
Tschmutowa, G. and Bock, H., Z. Naturforsch. B, 1976, vol. 31, no. 12, p. 1611.
Dewar, P.S., Ernstbrunner, E., Gilmore, J.R., Godfrey, N., and Mellor, J.M., Tetrahedron, 1974, vol. 30, no. 15, p. 2455.
Schweig, A. and Thon, N., Chem. Phys. Lett., 1976, vol. 38, no. 3, p. 482.
Mannafov, T.G., Mironov, S.F., Remizov, A.B., and Fishman, A.I., Zh. Prikl. Spektrosk., 1990, vol. 52, no. 1, p. 56.
Pauling, L., General Chemistry, San Francisco: Freeman, 1970.
Gilheany, D.G., Chem. Rev., 1994, vol. 94, no. 5, p. 1339.
Reed, A.E. and Weinhold, F., J. Am. Chem. Soc., 1986, vol. 108, no. 13, p. 3586.
Reed, A.E. and Schleyer, P.v.R., J. Am. Chem. Soc., 1990, vol. 112, no. 4, p. 1434.
Chierici, L., Lumbroso, H., and Passerini, R., Bull. Soc. Chim. Fr., 1955, no. 4, p. 686.
Chmutova, G.A. and Sorokina, L.A., Zh. Fiz. Khim., 1974, vol. 48, no. 4, p. 807.
Llabres, G., Baiwir, M., Christiaens, L., Denoel, J., Laitem, L., and Piette, J.-L., Can. J. Chem., 1978, vol. 56, no. 15, p. 2008.
Kalabin, G.A., Kushnarev, D.F., Bzhezovsky, V.M., and Tschmutova, G.A., Org. Magn. Reson., 1979, vol. 12, no. 10, p. 598.
Bzhezovskii, V.M., Kalabin, G.A., Chmutova, G.A., and Trofimov, B.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, no. 3, p. 586.
Kalabin, G.A. and Kushnarev, D.F., Zh. Strukt. Khim., 1979, vol. 20, no. 4, p. 617.
McFarlane, W. and Wood, R.J., J. Chem. Soc., Dalton Trans., 1972, no. 13, p. 1397.
Chmutova, G.A., Stroenie i reaktsionnaya sposobnost' organicheskikh soedinenii (Structure and Reactivity of Organic Compounds), Arbuzov, B.A., Ed., Moscow: Nauka, 1978, p. 227.
Hehre, W.J., Radom, L., Schleyer, P.v.R., and Pople, J.A., Ab initio Molecular Orbital Theory, New York: Wiley, 1986.
Møller, Ch. and Plesset, M.S., Phys. Rev., 1934, vol. 46, no. 4, p. 618.
Parr, R.G. and Yang, W., Density Functional Theory of Atoms and Molecules, New York: Oxford Univ. Press, 1989.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648.
Stephens, P.J., Delvin, C.F., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, no. 45, p. 11 623.
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., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Adamo, C., Clifford, S., Ocherski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., 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.A., Al-Laham, M.A., Peng, C.Y., Nanayakara, 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 98W, Rev. A.7, Pittsburgh: Gaussian, 1998.
Weinhold, F. and Carpenter, J.E., The Structure of Small Molecules and Ions, Naaman, R. and Vager, Z., Eds., New York: Plenum, 1988, p. 227.
Reed, A.E., Curtiss, L.A., and Weinhold, F., Chem. Rev., 1988, vol. 88, no. 6, p. 899.
Nemukhin, A.V. and Veinkhol'd, F., Ross. Khim. Zh., 1994, vol. 38, no. 6, p. 5.
Glendening, E.D., Reed, A.E., Carpenter, J.E., and Weinhold, F., GAUSSIAN 98W, Rev. A.7, NBO Ver.3.1, Pittsburgh: Gaussian, 1998.
Scott, A.P. and Radom, L., J. Phys. Chem., 1996, vol. 100, no. 41, p. 16 502.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bzhezovskii, V.M., Kapustin, E.G. Steric and Electronic Structure of Selenoanisole: A Quantum-Chemical Study. Russian Journal of General Chemistry 73, 54–60 (2003). https://doi.org/10.1023/A:1023422418192
Issue Date:
DOI: https://doi.org/10.1023/A:1023422418192