Abstract
Nonempirical RHF/STO-3G and 6-31G(d) studies on conformational behavior of tetrahydro-1,3- oxazine showed that interconversion between the axial (global minimum) and equatorial chair conformers can follow five independent pathways. The potential energy surface contains seven minima corresponding to chair and twist conformers, as well as seven transition states having sofa, half-chair, and symmetrical and unsym- metrical boat conformations. Additional potential barriers to interconversion, resulting from pyramidal inversion of the nitrogen atom, were also revealed.
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Latypova, F.N., Zorin, V.V., Zlotskii, S.S., Rakhmankulov, D.L., Karakhanov, R.A., Bartok, M., and Molnar, A., Acta Phys. Chem., 1981, vol. 27, p. 87.
Gurne, D. and Urbanski, T., J. Chem. Soc., 1959, p. 1912.
Gurne, D. and Urbański, T., Roczn. Chem., 1960, vol. 34, p. 881.
Riddel, F.G. and Lehn, J.M., J. Chem. Soc. B., 1968, p. 1224.
Kuznetsov, V.V., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, p. 1499.
Cookson, R.C. and Crabb, T.A., Tetrahedron, 1968, vol. 24, p. 2385.
Allingham, Y., Cookson, R.C., Crabb, T.A., and Vary, S., Tetrahedron, 1968, vol. 24, p. 4625.
Samitov, Yu.Yu., Unkovskii, B.V., Boiko, I.P., Zhuk, O.I., and Malina, Yu.F., Zh. Org. Khim., 1973, vol. 9, p. 193.
Lehn, J.M., Linscheid, P., and Riddel, F.G., Bull. Soc. Chim.Fr., 1968, p. 1172.
Ferguson, I.J, Katritzky, A.R., and Reed, D.M., J. Chem. Soc., Perkin Trans. 2, 1977, p. 818.
Booth, H. and Lemieux, R.U., Can. J. Chem., 1971, vol. 49, p. 777.
Jones, R.A.Y., Katritzky, A.R., and Trepanier, D.L., J. Chem. Soc. B, 1971, p. 1300.
Halls, P.J., Jones, R.A.Y., Katritzky, A.R., Snarey, M., and Trepanier, D.L., J. Chem. Soc. B, 1971, p. 1320.
Jones, R.A.Y., Katritzky, A.R., Richards, A.C., Saba, S., Sparrow, A.J., and Trepanier, D.L., J. Chem. Soc., Chem. Commun., 1972, p. 673.
Cook, M.J., Jones, R.A.Y., Katritzky, A.R., Moreno Manas, M., Richards, A.C., Sparrow, A.J., and Trepanier, D.L., J. Chem. Soc., Perkin Trans. 2, 1973, p. 325.
Blackburne, I.D., Duke, R.P., Jones, R.A.Y., Katritzky, A.R., and Record, K.A.F., J. Chem. Soc., Perkin Trans. 2, 1973, p. 332.
Kuramshina, A.E., Faizullin, A.A., Bochkor, S.A., and Kuznetsov, V.V., Bash. Khim. Zh., 2004, no. 11, p. 81.
Internal Rotation in Molecules, Orville-Thomas, W.J., Ed., London: Wiley, 1974. Translated under the title Vnutrennee vrashchenie molekul, Moscow: Mir, 1975, p. 355.
HyperChem 7.01. Trial version, www.hyper.com.
Zefirov, N.S. and Palyulin, V.A., Dokl. Akad. Nauk SSSR, 1980, vol. 252, p. 111.
Zefirov, N.S., Dashevskaya, E.E., and Palyulin, V.A., Dokl. Akad. Nauk SSSR, 1987, vol. 292, p. 1380.
Zefirov, N.S., Palyulin, V.A., and Dashevskaya, E.E., J. Phys. Org. Chem., 1990, vol. 3, p. 147.
Kuznetsov, V.V., Kuramshina, A.E., and Bochkor, S.A., Fundam. Issled., 2006, vol. 3, p. 87.
Mazitova, E.G., Kuramshina, A.E., and Kuznetsov, V.V., Russ. J. Org. Chem., 2004, vol. 40, p. 588.
Kuramshina, A.E., Bochkor, S.A., and Kuznetsov, V.V., Russ. J. Org. Chem., 2006, vol. 42, p. 612.
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Original Russian Text © V.V. Kuznetsov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 1, pp. 117–120.
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Kuznetsov, V.V. Ab Initio conformational analysis of tetrahydro-1,3-oxazine. Russ J Org Chem 46, 117–121 (2010). https://doi.org/10.1134/S1070428010010112
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DOI: https://doi.org/10.1134/S1070428010010112