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Chemistry of Heterocyclic Compounds

, Volume 35, Issue 8, pp 928–934 | Cite as

Conformational analysis of substituted 1,3,2-oxazaborinanes

  • V. V. Kuznetsov
Article

Abstract

The empirical (MM2) and semiempirical (AM1, MNDO) methods were used to calculate the energy of unsubstituted and 2-, 3-, 5-, 3,5-, and 2,3,5-substituted 1,3,2-oxazaborinanes with complete geometrical optimization. The major minimum on the potential energy surface corresponds to the sofa conformation. The number of other local minima relates to the half-chair and 1,4-, 3,6-, and 2,5-twist conformations. The experimental ΔG0 value for 5-methyl group on the C(5) carbon atom was determined by comparisom of calculated and experimental spin-spin coupling constants.

Keywords

Organic Chemistry Carbon Atom Potential Energy Energy Surface Local Minimum 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    A. I. Gren' and V. V. Kuznetsov,Chemistry of Cyclic Borate Esters [in Russian], Naukova Dumka, Kiev (1988).Google Scholar
  2. 2.
    A. R. Kalyuskii, Author's Abstract of Chemical Sciences Candidate's Dissertation, Odessa (1990).Google Scholar
  3. 3.
    A. R. Kalyuskii, V. V. Kuznetsov, Yu. E. Shapiro, S. A. Bochkor, and A. I. Gren',Khim. Geterotsikl. Soedin., No. 10, 1424 (1990).Google Scholar
  4. 4.
    A. R. Kalyuskii, V. V. Kuznetsov, O. S. Timofeev, and A. I. Gren',Zh. Obshch. Khim.,60, 2093 (1990).Google Scholar
  5. 5.
    A. R. Kalyuskii, V. V. Kuznetsov, Yu. É. Brusilovskii, V. Ya. Gorbatyuk, M. G. Glukhova, and A. I. Gren',Zh. Org. Khim.,26, 2498 (1990).Google Scholar
  6. 6.
    A. R. Kalyuskii, V. V. Kuznetsov, and A. I. Gren',Zh. Obshch. Khim.,61, 1351 (1991).Google Scholar
  7. 7.
    A. R. Kalyuskii, V. V. Kuznetsov, N. E. Kruglyak, I. V. Yudanova, L. P. Trigub, and A. I. Gren]Dep. v VINITI, No. 1113-V90; Ref. Zh. Khim., No. 11, B1095 (1990).Google Scholar
  8. 8.
    R. C. Bingham, M. J. S. Dewar, and D. H. Lo,J. Am. Chem. Soc.,97, 1294 (1975).CrossRefGoogle Scholar
  9. 9.
    P. Birner and H. Hofmann,Int. J. Quant. Chem.,21, 833 (1982).CrossRefGoogle Scholar
  10. 10.
    N. L. Allinger,J. Am. Chem. Soc.,99, 8127 (1977).CrossRefGoogle Scholar
  11. 11.
    M. J. S. Dewar, E. G. Zoebisch, E. P. Healy, and J. J. P. Stewart,J. Am. Chem. Soc.,107, 3902 (1985).CrossRefGoogle Scholar
  12. 12.
    M. J. S. Dewar, C. Jie, and E. C. Zoebisch,Organometallics,7, 53 (1988).Google Scholar
  13. 13.
    M. J. S. Dewar and W. Thiel,J. Am. Chem. Soc.,99, 4899 (1977).CrossRefGoogle Scholar
  14. 14.
    M. J. S. Dewar and M. L. McKee,J. Am. Chem. Soc.,99, 5231 (1977).Google Scholar
  15. 15.
    S. Kuribayashi,Bull. Soc. Chem. Japan,46, 1045 (1973).Google Scholar
  16. 16.
    R. Seip and H. Seip,J. Mol. Struct.,28, 441 (1975).CrossRefGoogle Scholar
  17. 17.
    V. V. Kuznetsov, A. R. Kalyuskii, and A. I. Gren',Khim. Geterotsikl. Soedin., No. 1, 106 (1996).Google Scholar
  18. 18.
    P. L. Durette and D. Horton,Org. Magn. Reson.,3, 417 (1971).CrossRefGoogle Scholar
  19. 19.
    M. L. Huggins,J. Am. Chem. Soc.,75, 4123 (1953).CrossRefGoogle Scholar
  20. 20.
    N. S. Zefirov, V. S. Blagoveshchenskii, I. V. Kazimirchik, and O. P. Yakovleva,Zh. Org. Khim.,7, 594 (1971).Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

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  • V. V. Kuznetsov

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