Conclusions
-
1.
In allyl compounds CH2=CH-CH2-XH3 the conjugation effects intensify in the sequence X=C, Si, Ge, Sn, and Pb, and are expressed in the strongest degree in gauche -conformers. They are basically conditioned by the interaction of the π orbital of the C=C bond with the a orbitals of group -XH3, which is realized only when the coplanarity of the molecules is disturbed and when the restriction of the symmetry is lifted.
-
2.
According to calculated data, this interaction has little influence on the distribution of electron density, on the sequences of bonds, and on the conformational equilibrium in the fundamental state, but leads to a strong change in the MO system, and must be reflected, first of all, in UV spectra, in the IP's, and in the rates of electrophilic and nucleophilic reactions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
P. P. Shorygin and Z. B. Alaune, Zh. Fiz. Khim.,34, 2299 (1960).
P. P. Shorygin, V. A. Petukhov, and L. G. Stolyarova, Dokl, Akad. Nauk SSSR,154, 441 (1964).
P. P. Shorygin, V. A. Petukhov, A. Kh. Khomenko, and B. V. Lopatin, Zh. Fiz. Khim.,42, 1584 (1968).
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).
A. Schweig and U. Weidner, J. Organomet. Chem.,99, 4899 (1977).
P. K. Bischof, M. J. S. Dewar, D. W. Goodman, and T. B. Jones, J. Organomet. Chem.,82, 89 (1974).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2764–2769, December, 1987.
Rights and permissions
About this article
Cite this article
Burshtein, K.Y., Shorygin, P.P. Quantum chemical investigation of allyl compounds with group iv elements. Communication I. Electron structure of molecules in the fundamental state. Russ Chem Bull 36, 2563–2567 (1987). https://doi.org/10.1007/BF00957235
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00957235