Abstract
The structures of possible intermediates and transition states on the potential energy surface for the isomerization of methanimine oxide into formamide were determined by UHF/6-311G(3d) quantum-chemical calculations. Two possible reaction channels were revealed. The same processes were studied by the direct molecular mechanics method which also revealed two reaction channels. The time range of the examined dynamic processes was estimated at 90–300 fs.
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REFERENCES
Zewail, A.H., Femtochemistry: Ultrafast Dynamics of the Chemical Bond. Singapore: World Scientific, 1994, vols. 1, 2.
Femtosecond Chemistry, Manz, J. and Woste, L., Eds., Weinheim: VCH, 1995.
Zhong, D., Diau, E.W.-G., Bernhardt, T.M., De Feyter, S., Roberts, J.D., and Zewail, A.H., Chem. Phys. Lett., 1998, vol. 298, p. 129.
Herek, J.L., Materny, A., and Zewail, A.H., Chem. Phys. Lett., 1994, vol. 228, p. 15.
Dietz, H. and Engel, V., Chem. Phys. Lett., 1996, vol. 255, p. 258.
Andersson, L.M., Karlsson, H.O., Goscinski, O., Berg, L.-E., Beutter, M., and Hansson, T., Chem. Phys., 1999, vol. 241, p. 43.
Sarkisov, O.M., Tovbin, D.V., Lozovoy, V.V., Gos-tev, F.E., Titov, A.A., Antipin, S.A., and Uman-skiy, S.Ya., Chem. Phys. Lett., 1999, vol. 303, p. 458.
Lozovoy, V.V., Antipin, S.A., Gostev, F.E., Ti-tov, A.A., Tovbin, D.V., Sarkisov, O.M., Vetchin-kin, A.S., and Umanskiy, S.Ya., Chem. Phys. Lett., 1998, vol. 284, p. 221.
Zhang, J.Z., Schwartz, B.J., King, J.C., and Harris, C.B., J. Am. Chem. Soc., 1992, vol. 114, p. 10921.
Felker, P.M., Lambert, Wm.R., and Zewail, A.H., J. Chem. Phys., 1982, vol. 77, p. 1603.
Antipin, S.A., Petrukhin, A.N., Gostev, F.E., Marev-tsev, V.S., Titov, A.A., Barachevsky, V.A., Stro-kach, Yu.P., and Sarkisov, O.M., Chem. Phys. Lett., 2000, vol. 331, p. 378.
Dzhemesyuk, O.A., Antipin, S.A., Gostev, F.E., Fedo-rovich, I.B., Sarkisov, O.M., and Ostrovskii, M.A., Dokl. Ross. Akad. Nauk, 2002, vol. 382, p. 699.
Minkin, V.I., Simkin, B.Ya., and Minyaev, R.M., Teoriya stroeniya molekul (Theory of Molecular Structure), Rostov-on-Don: Feniks, 1997, p. 558.
Minyaev, R.M., Usp. Khim., 1994, vol. 63, p. 939.
Car, R. and Parinello, M., Phys. Rev. Lett., 1985, vol. 55, p. 2471.
Marx, D. and Huter, J., Ab initio Molecular Dynamics: Theory and Implementation in Modern Methods and Algorithms of Quantum Chemistry, Grotendorst, J., Ed., Julich, 2000, p. 149.
Tuckerman, E., Ungar, P.J., von Rosenvinge, T., and Klein, M.L., J. Phys. Chem., 1996, vol. 100, p. 12788.
Aida, M., Yamataka, H., and Dupuis, M., Theor. Chem. Acc., 1999, vol. 102, p. 262.
Skokov, S. and Wheeler, R.A., J. Phys. Chem. A, 2000, vol. 104, p. 6314.
Truhlar, D.G., The Reaction Path in Chemistry: Current Approaches and Perspectives, Heidrich, D., Ed., Dord-recht: Kluwer, 1995, p. 229.
Steckler, R., Thurman, G.M., Watts, J.D., and Bart-lett, R.J., J. Chem. Phys., 1997, vol. 106, p. 3926.
Wei, D. and Salahub, D.R., J. Chem. Phys., 1997, vol. 106, p. 6086.
Ishikawa, Y. and Binning, Jr.R.C., Chem. Phys. Lett., 2002, vol. 358, p. 509.
Doubleday, C., Bolton, K., and Hase, W.L., J. Phys. Chem. A, 1998, vol. 102, p. 3648.
Li, G. and Hase, W.L., J. Am. Chem. Soc., 1999, vol. 121, p. 7124.
Zhang, X., Ding, Y., Li, Z., Huang, X., and Sun, Ch., Chem. Phys. Lett., 2000, vol. 330, p. 577.
Li, Sh., Yu, X., Xu, Zh., Li, Z., and Sun, Ch., J. Mol. Struct. (Theochem), 2001, vol. 540, p. 221.
Bolton, K., Hase, W.L., Schlegel, H.B., and Song, R., Chem. Phys. Lett., 1998, vol. 288, p. 621.
Peslherbe, G.H., Wang, H., and Hase, W.L., J. Am. Chem. Soc., 1996, vol. 118, p. 2257.
Splitter, J. and Calvin, M., J. Org. Chem., 1965, vol. 30, p. 3427.
Spence, G.G., Taylor, E., and Buchardt, O., Chem. Rev., 1970, vol. 70, p. 231.
Shinzawa, K. and Tanaka, I., J. Phys. Chem., 1964, vol. 68, p. 1205.
Koyano, K. and Tanaka, I., J. Phys. Chem., 1965, vol. 69, p. 2545.
Koyano, K., Suzuki, H., Mori, Y., and Tanaka, I., Bull. Chem. Soc. Jpn., 1970, vol. 43, p. 3582.
Krishan, K. and Singkh, Kh., Izv. Akad. Nauk SSSR, Ser. Khim., 1974, p. 1404.
Fukui, K., Acc. Chem. Res., 1981, vol. 14, p. 363.
Schmidt, M.W., Baldridge, K.K., Boatz, J.A., El-bert, S.T., Gordon, M.S., Jensen, J.H., Koseki, H., Matsunaga, N., Nguyen, K.A., Su, S.J., Windus, T.L., Dupuis, M., and Montgomery, A., J. Comput. Chem., 1993, vol. 14, p. 1347.
Frisch, M.J, Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, T., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewski, V.G., Ortiz, J.V., Fores-man, J.B., Cioslowski, J., Stefanov, B.B., Nanayak-kara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, W., Wong, M.W., Andres, J.L., Replogle, E.S., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., Defrees, D.J., Baker, J., Stewart, J.P., Head-Gordon, M., Gonzalez, C., and Pople, J.A., Gaussian 94, Revision D, Pittsburgh PA: Gaussian, 1995.
HyperChem 5.0 for Windows, Hypercube, 1994-1995.
Allen, M.P. and Tildesley, D.J., Computer Simulation of Liquids, Oxford: Clarendon, 1987, p. 385.
Doubleday, C., Chem. Phys. Lett., 1995, vol. 233, p. 509.
Doubleday, C., Bolton, K., Peslherbe, G.H., and Hase, W.L., J. Am. Chem. Soc., 1996, vol. 118, p. 9922.
Gillespie, R.J., Molecular Geometry, New York: Rein-hold, 1972.
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Aminova, R.M., Ermakova, E.A. Dynamic Intramolecular Rearrangements with Proton Transfer in Methanimine Oxide. Russian Journal of Organic Chemistry 40, 837–846 (2004). https://doi.org/10.1023/B:RUJO.0000044547.70022.ee
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DOI: https://doi.org/10.1023/B:RUJO.0000044547.70022.ee