Abstract
The dependence of the strain energy on the distance between the nitrogen and silicon atoms was studied for the 1-methyl-2-carbasilatrane molecule within the framework of the Westheimer method. For models with the postulated silicon coordination numbers of 5 and 4, respectively, Si...N distances of 2.31 Å (19.4 kcal/mole) and 2.41 Å (32.4 kcal/mole) correspond to the minimum of the conformational energy of the endo form. The exo form is the most stable when the distance between the Si and N atoms is 3.10 A, and it is also the least strained system (1.8 kcal/mole). Since 1-methy1-2-carbasilitrane exists only in the endo form, the stability of the latter can be justified only under the condition that the energy of the transannular Si←N interaction exceeds 17.6 kcal/mole.
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M. G. Voronkov, I. S. Emel'yanov, V. M. D'yakov, V. Yu. Vitkovskii, L. V. Kapranova, and V. P. Baryshok, Khim. Geterotsikl. Soedin., No. 10, 1344 (1976).
M. G. Voronkov, V. F. Sidorkin, V. A. Shagun, V. A. Pestunovich, and G. I. Zelchan, Khim. Geterotsikl. Soedin., No. 5, 715 (1975).
F. P. Boer, and I. W. Turlen, J. Am. Chem. Soc.,91, 4135 (1969).
V. A. Pestunovich, M. G. Voronkov, G. I. Zelchan, É. Ya. Lukevits, L. I. Libert, A. I. Egorochkin, and A. I. Burov, Khim. Geterotsikl. Soedin., No. 1, 339 (1970).
V. G. Dashevskii, Zh. Strukt. Khim.,9, 289 (1968).
V. P. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments [in Russian], Khimiya, Leningrad (1963).
N. C. Cohen, Tetrahedron,27, 789 (1971).
N. L. Allinger, M. Tribble, M. A. Miller, and D. H. Wertz, J. Am. Chem. Soc.,93, 1637 (1971).
A. I. Kitugorodskii (Kitaigorodsky) and V. G. Dashevskii (Dashevsky), Tetrahedron,24, 5917 (1968).
N. L. Allinger, J. A. Hirsch, M. A. Miller, and J. F. Timinski, J. Am. Chem. Soc.,90, 5773 (1968).
W. Airen, C. Glidwell, A. G. Robiette, and G. M. Sheldrick, J. Mol. Struct.,8, 413 (1971).
or]M. R. Yagudaev, E. M. Popov, P. P. Yakovlev, and Yu. N. Sheinker, Izv. Akad. Nauk SSSR, Ser. Khim., 1189 (1964).
E. E. Shestakov, Author's Abstract of Master's Dissertation, Leningrad (1973).
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See [1] for communication XLVIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1347–1350, October, 1976.
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Sidorkin, V.F., Shagun, V.A., Pestunovich, V.A. et al. Atranes. Chem Heterocycl Compd 12, 1117–1120 (1976). https://doi.org/10.1007/BF00945593
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DOI: https://doi.org/10.1007/BF00945593