Skip to main content
SpringerLink
Log in

Analysis of the conformational composition of the 4,5- and 5,6-dimethyl-1,3,2-oxazaborinane stereoisomers

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An energy for the molecules of cis and trans 4,5- and 5,6-dimethyl-1,3,2-oxazaborinanes, and of model 1,3,2-oxazaborinanes and tetrahydro-1,3-oxazines with full geometric optimization has been calculated using empirical (MM2) and semiempirical (AM1) methods. From a comparison of experimental and calculated coupling constants and the relative energies of individual conformers it follows that molecules of the cyclic boron esters form a multicomponent equilibrium system, comprizing sofa and half-chair forms with an equatorial orientation of the N−H bond.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. R. Kalyuskii, V. V. Kuznetsov, Yu. E. Shapiro, S. A. Bochkor, and A. I. Gren',Khim. Geterotsikl. Soedin., No. 10, p. 1424 (1990).

    Google Scholar 

  2. A. R. Kalyuskii, Authors summary of dissertation for candidate of chemical sciences, Odessa (1990).

  3. A. R. Kalyuskii, V. V. Kuznetsov, O. S. Timofeev, and A. I. Gren'Zh. Obshch. Khim.,60, 2093 (1990).

    Google Scholar 

  4. A. P. Kalyuskii, V. V. Kuznetsov, and A. I. Gren',Zh. Obshch. Khim.,61, 1351 (1991).

    Google Scholar 

  5. A. R. Kalyuskii, V. V. Kuznetsov, Yu. E. Brusilovskii, V. Ya. Gorbatyuk, M. G. Glukhova, and A. I. Gren',Zh. Org. Khim.,26, 2498 (1990).

    Google Scholar 

  6. A. R. Kalyuskii, V. V. Kuznetsov, N. E. Kruglyak, I. V. Yudanova, L. P. Trigub, and A. I. Gren', Deposition in VINITI No. 1113-V90;Ref. Zh. Khim., No. 11, B1095 (1990).

    Google Scholar 

  7. R. C. Bingham, M. J. S. Dewar, and D. H. Lo,J. Am. Chem. Soc.,97, 1294 (1975).

    Google Scholar 

  8. P. Birner and H. Hofmann,Int. J. Quant. Chem.,21, 833 (1982).

    Google Scholar 

  9. N. L. Allinger,J. Am. Chem. Soc.,99, 8127 (1977).

    Google Scholar 

  10. M. J. S. Dewar, E. G. Zoebisch, E. P. Healy, and J. J. P. Stewart,J. Am. Chem. Soc.,107, 3902 (1985).

    Google Scholar 

  11. M. J. S. Dewar, C. Jie, and E. G. Zoebisch,Organometallics,7, 513 (1988).

    Google Scholar 

  12. A. I. Gren' and V. V. Kuznetsov,Chemistry of Cyclic Esters of Boric Acids [in Russian], Naukova Dumka, Kiev (1988).

    Google Scholar 

  13. R. Seip and H. Seip,J. Mol. Struct.,28, 441 (1975).

    Google Scholar 

  14. W. J. Orville-Thomas (editor),Internal Rotation in Molecules, cited in [Russian translation], Mir, Moscow (1977), p. 373.

    Google Scholar 

  15. V. V. Kuznetsov, A. R. Kalyuskii, and A. I. Gren',Khim. Geterotsikl. Soedin., No. 1, 106 (1996).

    Google Scholar 

  16. Yu. Yu. Samitov, B. V. Unkovskii, I. P. Boiko, O. I. Zhuk, and Yu. F. Malina,Zh. Org. Khim.,9, 193 (1973).

    Google Scholar 

  17. Yu. Yu. Samitov, O. I. Zhuk, B. V. Unkovskii, I. P. Boiko, and Yu. F. Malina,Zh. Org. Khim.,9, 201, (1973).

    Google Scholar 

  18. O. I. Danilova, Yu. Yu. Samitov, I. P. Boiko, T. O. Bordyukova, and B. V. Unkovskii, Deposition in ONIITEKhIM, No. 1056khp-D80;Ref. Zh. Khim., No. 9, B329 (1981).

    Google Scholar 

  19. F. N. Latypova, V. V. Zorin, S. S. Zlotskii, D. L. Rakhmankulov, R. A. Karakhanov, M. Bartok, and A. Molnar,Acta Phys. Chem.,27, 87 (1981).

    Google Scholar 

  20. F. A. Alimirzoev, A. U. Stepanyants, F. N. Latypova, and B. V. Unkovskii, Deposition in ONIITEKhIM, No. 3093/79 dep;Ref. Zh. Khim., No. 3, B325 (1980).

    Google Scholar 

  21. O. I. Danilova, Yu. Yu. Samitov, I. P. Boiko, T. O. Bordyukova, and B. V. Unkovskii, Deposition in ONIITEKhIM, No. 1055khp-D80;Ref. Zh. Khim., No. 9, B330 (1981).

    Google Scholar 

  22. O. I. Danilova, Yu. Yu. Samitov, I. P. Boiko, T. O. Bordyukova, and B. V. Unkovskii, Deposition in ONIITEKhIM, No. 539, khp-D81;Ref. Zh. Khim., No. 24, B 392 (1981).

    Google Scholar 

  23. O. I. Danilova, Yu. Yu. Samitov, I. P. Boiko, and B. V. Unkovskii, Deposition in ONIITEKhIM, No. 1058 khp-D80;Ref. Zh. Khim., No. 9, B328 (1981).

    Google Scholar 

  24. H. Booth and R. U. Lemieux,Can. J. Chem.,49, 777 (1971).

    Google Scholar 

  25. M. J. Cook, R. A. Y. Jones, A. R. Katritzky, M. M. Monas, A. C. Richards, A. J. Sparrow, and D. L. Trepanier,J. Chem. Soc., Perkin Trans. 2, No. 4, 325 (1973).

    Google Scholar 

  26. P. L. Durette and D. Horton,Org. Magn. Res.,3, 417 (1971).

    Google Scholar 

  27. M. L. Huggins,J. Am. Chem. Soc.,75, 4123 (1953).

    Google Scholar 

  28. O. V. Shishkin, A. S. Polyakova, Yu. T. Struchkov, and S. M. Desenko,Mendeleev Commun., No. 5, 182 (1994).

    Google Scholar 

  29. O. V. Shishkin,Izv. Russ. Akad. Sci., Ser. Khim., No. 12, 2095 (1997).

    Google Scholar 

Download references

Authors
  1. V. V. Kuznetsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

A. V. Bogatskii Institute of Physics and Chemistry, Ukrainian Academy of Sciences, Odessa 270080, Ukraine; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1176–1184, September, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kuznetsov, V.V. Analysis of the conformational composition of the 4,5- and 5,6-dimethyl-1,3,2-oxazaborinane stereoisomers. Chem Heterocycl Compd 35, 1033–1040 (1999). https://doi.org/10.1007/BF02251794

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02251794

Keywords

Search

Navigation