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X-ray structural investigation of gossypol and its derivatives XXIX. Molecular and crystal structure of a complex of gossypolic acid lactone with acetic acid

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Abstract

The lactone of gossypolic acid, obtained by the demethylation of the tetramethyl ether of gossypolic acid, forms with acetic acid a stable complex having the 1∶4 composition. The crystallographic parameters of single crystals are as follows:a=20.251(2) Å, b=12.028(3) Å, c=15.934(4) Å, V=3881.2(2.3) Å3,Z=4, D calc=1.32 g/cm3, sp. gr. Pbcn. The molecule is characterized by considerable strain because of the formation of the five-membered lactone ring the atoms of which are coplanar with the atoms of the naphthyl fragment. Unlike the clathrates of racemic gossypol and dianilinegossypol, the gossypolic acid lactone — acetic acid comples does not belong to the type of clathrate inclusion compounds.

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References

  1. S. A. Talipov, B. T. Ibragimov, G. N. Tishchenko, T. F. Aripov, G. B. Nazarov, B. V. Strokopytov, and K. M. Polyakov,Kristallografiya,33, 384 (1988).

    Google Scholar 

  2. S. A. Talipov, B. T. Ibragimov, G. N. Tishchenko, and T. F. Aripov,Kristallografiya,34, 327 (1989).

    Google Scholar 

  3. B. T. Ibragimov, S. A. Talipov, T. F. Aripov, and A. S. Sadykov,J. Inclusion Phenomena,8, 323 (1990).

    Google Scholar 

  4. B. T. Ibragimov, S. A. Talipov, and M. Gdaniec,J. Inclusion Phenomena,8, 333 (1990).

    Google Scholar 

  5. B. T. Ibragimov, S. A. Talipov, and M. Gdaniec,J. Inclusion Phenomena,8, 409 (1990).

    Google Scholar 

  6. N. I. Baram, F. G. Kamaev, Kh. L. Ziyaev, L. Biktimirov, A. I. Ismailov, and B. T. Ibragimov,Khim. Prir. Soedin., 650 (1988).

  7. K. M. Beketov, B. T. Ibragimov, and S. A. Talipov,Khim. Prir. Soedin., 58 (1994).

  8. G. B. Nazarov, B. T. Ibragimov, and T. F. Aripov,Khim. Prir. Soedin., 661 (1988).

  9. B. T. Ibragimov, K. M. Beketov, S. A. Talipov, I. Duax, and F. Strong,Khim. Prir. Soedin., 676 (1995).

  10. B. T. Ibragimov, K. M. Beketov, S. A. Talipov, and R. G. Mardanov,Khim. Prir. Soedin. 682 (1995).

  11. N. I. Baram, A. I. Ismailov, V. B. Leont'ev, F. G. Kamaev, and A. A. Sadykov, Dokl. Akad. Nauk SSSR,195, 1097 (1970).

    Google Scholar 

  12. F. G. Kamaev, N. I. Baram, A. I. Ismailov, V. B. Leont'ev, and A. A. Sadykov,Izv. Akad. Nauk SSSR, Ser. Khim., 1003 (1979).

  13. L. Pouling,The Nature of the Chemical Bond, Cornell University Press, New York (1960).

    Google Scholar 

  14. V. I. Ponomarev, O. S. Filipenko, and L. O. Atovmyan,Kristallografiya,21, 392 (1976).

    Google Scholar 

  15. R. Adams and T. A. Geissman,J. Am. Chem. Soc.,60, 2166 (1938).

    Google Scholar 

  16. P. C. Meltzer, W. H. Bickford, and J. I. Lambert,J. Org. Chem. 50, No. 17, 3121 (1985).

    Google Scholar 

  17. G. M. Sheldrick,Acta Crystallogr.,A46, 467 (1990).

    Google Scholar 

  18. G. M. Sheldrick, SHELX-76. Program for Crystal Structure Determination, Cambridge University Press (1976).

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Authors
  1. S. A. Talipov
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  2. R. G. Mardanov
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  3. B. T. Ibragimov
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  4. K. M. Beketov
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  5. O. Kh. Kholbekov
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Additional information

A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Ul. Akad. Kh. Abdullaeva, 83. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 458–463, July–August, 1999.

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Talipov, S.A., Mardanov, R.G., Ibragimov, B.T. et al. X-ray structural investigation of gossypol and its derivatives XXIX. Molecular and crystal structure of a complex of gossypolic acid lactone with acetic acid. Chem Nat Compd 35, 409–414 (1999). https://doi.org/10.1007/BF02282505

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  • DOI: https://doi.org/10.1007/BF02282505

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