Abstract
The electron conformations and tautomeric transformations of the gossypol molecule have been investigated by the MO LCAO method in the AMI approximation. On the basis of an analysis of the electronic structures of 24 model molecules, each forming, as it were, a component part of gossypol, the role of dynamic intramolecular processes in its tautomeric interconversions has been elucidated. The exceptional role of intramolecular hydrogen bonds in the formation of the electron patterns in different structural forms has been shown. The correlation of the dependence of the chemical shifts of the13C nuclei on the electron density distribution in the structural forms of gossypol has been studied.
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References
V. I. Minkin B. Ya. Simkin, and R. M. Minyaev, The Quantum Chemistry of Organic Compounds. Reaction Mechanisms [in Russian], Khimiya, Moscow (1986).
R. Adams, T. A. Geissman, and J. D. Edwards, Chem. Rev.,60, 555 (1960).
F. G. Kamaev, N. I. Baram, A. I. Ismailov, V. B. Leont'ev, and A. S. Sadykov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1003 (1979).
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc.,107, 3092 (1985).
R. Fletcher and M. J. D. Powell, Comput. J.,6, 163 (1963); W. C. Davidon, Comput. J.,10, 406 (1968).
B. T. Ibragimov, The Crystal Chemistry of Gossypol [in Russian], Author's abstract of dissertation ... Doctor of Chemical Sciences [in Russian], Moscow (1991).
L. V. Vilkov, V. S. Mastryukov, and N. I. Sadova, The Determination of the Geometric Structures of Free Molecules [in Russian], Khimiya, Leningrad (1978).
A. L. Markman and V. P. Rzhekhin, Gossypol and its Derivatives [in Russian], Pishchevaya Promyshlennost’, Moscow (1965).
L. Biktimirov, N. I. Baram, A. I. Ismailov, F. G. Kamaev, and V. B. Leont'ev, Khim. Prir. Soedin., 286 (1975).
N. I. Baram, A. I. Ismailov, V. B. Leont'ev, F. G. Kamaev, and A. S. Sadykov, Dokl. Akad. Nauk SSSR,195, No. 5, 1097 (1970).
N. D. Abdullaev, A. A. Tyshchenko, 1. P. Nazarova, N. T. Ul'chenko, M. R. Yagudaev, and A. I. Glushenkova, Khim. Prir. Soedin., 166 (1990).
C. Zhiking, Theor. Chim. Acta,66, 365 (1985).
N. A. Ogorodnikova, A. A. Koridze, É. I Fedin, and P. V. Petrovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2047 (1983).
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Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 517–529, July–August, 1996. Original article submitted June 23, 1993; revision submitted May 16, 1996.
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Ashirmatov, M.A., Abdullaev, N.D. Quantum-chemical investigation of some features of the interconversions of the gossypol molecule. Chem Nat Compd 32, 513–522 (1996). https://doi.org/10.1007/BF01372602
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DOI: https://doi.org/10.1007/BF01372602