Skip to main content
SpringerLink
Log in

Conformational Analysis of 5-Methyl-1,3-oxathiane

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Computer simulation of conformational transformations of 5-methyl-1,3-oxathiane at the DFT PBE/3ζ, RI-MP2/λ2, and HF/6-31++G(d,p) levels of theory has shown that the interconversion between the equatorial (global minimum) and axial chair conformers occurs along several independent pathways through five flexible forms. Nine transition states corresponding to different half-chair forms, as well as symmetrical and unsymmetrical boat conformers, have been localized on the potential energy surface. The free conformational energy of the methyl group has been estimated at 0.9–1.0 kcal/mol by comparison of the calculated and experimental vicinal coupling constants in the 1H NMR spectra.

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. Kleinpeter, E., Adv. Heterocycl. Chem. 2004, vol. 86, p. 75.

    Google Scholar 

  2. Pihlaya, K., Passanen, P., and Wähäsilta, J., Org. Magn. Reson. 1979, vol. 12, p. 331.

    Article  Google Scholar 

  3. Rakhmankulov, D.L., Zorin, V.V., Latypova, F.N., Zlotskii, S.S., and Karakhanov, R.A., Russ. Chem. Rev. 1983, vol. 52, p. 350.

    Article  Google Scholar 

  4. Kuznetsov, V.V., Russ. J. Gen. Chem. 2012, vol. 82, p. 869.

    Article  CAS  Google Scholar 

  5. Stuparu, M., Grosu, I., Muntean, L., Ple, G., Cismas, C., Terec, A., Nan, A., and Mager, S., Monatsh. Chem. 2004, vol. 135, p. 89.

    Article  CAS  Google Scholar 

  6. Terez, A., Grosu, I., Ple, G., Muntean, L., and Mager, S., Heterocycles 2003, vol. 60, p. 1477.

    Article  Google Scholar 

  7. Haramoto, Y. and Kamogava, H., Mol. Cryst. Liq. Cryst. 1985, vol. 131, p. 201.

    Article  CAS  Google Scholar 

  8. Palmer, C.J. and Casida, J.E., J. Agric. Food Chem., 1995, vol. 43, p. 498.

    Article  CAS  Google Scholar 

  9. Solladié-Cavallo, A., Balaz, M., Salisova, M., and Welter, R., J. Org. Chem., 2003, vol. 68, p. 6619.

    Article  CAS  PubMed  Google Scholar 

  10. Saito, B. and Katsuki, T., Chilarity, 2003, vol. 15, p. 24.

    CAS  Google Scholar 

  11. Aggarwal, V.K., Lattanzi, A., and Fuentes, D., Chem. Commun. 2002, p. 2534.

    Google Scholar 

  12. Nakano, H., Okuyama, Y., Yanagida, M., and Yongo, H., J. Org. Chem., 2001, vol. 66, p. 620.

    Article  CAS  PubMed  Google Scholar 

  13. Fulton, J.R., Aggarwal, V.K., and Vicente, J., Eur. J. Org. Chem. 2005, p. 1467.

    Google Scholar 

  14. Crich, D. and Li, L., J. Org. Chem., 2009, vol. 74, p. 773.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Chacón-Garsía, L., Lagunas-Rivera, S., Pérez-Estrada, S., Vargas-Días, M.E., Joseph-Nathan, P., Tamariz, J., and Zepeda, L.G., Tetrahedron Lett. 2004, vol. 45, p. 2141.

    Article  CAS  Google Scholar 

  16. De Wolf, N., Verschoor, G.C., and Romers, C., Acta Crystallogr., Sect. B 1972, vol. 28, p. 2424.

    Article  Google Scholar 

  17. Turyanskaya, A.M., Novikov, A.N., Verkhivker, G.M., and Kuznetsov, V.V., Russ. J. Gen. Chem. 2001, vol. 71, p. 1487.

    Article  CAS  Google Scholar 

  18. Turyanskaya, A.M. and Kuznetsov, V.V., Chem. Heterocycl. Compd. 2002, vol. 38, p. 607.

    Article  CAS  Google Scholar 

  19. Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., Int. Ed. 2005, vol. 54, p. 820.

    Article  CAS  Google Scholar 

  20. HyperChem 8.0. http://www.hyper.com

  21. Friebolin, H., Schmid, H.G., Kabuss, S., and Faisst, W., Org. Magn. Reson. 1969, vol. 1, p. 67.

    Article  Google Scholar 

  22. Kuznetsov, V.V., Russ. J. Org. Chem. 2014, vol. 50, p. 1227.

    Article  CAS  Google Scholar 

  23. Haasnoot, C.A.G., de Leeuw, F.A.A.M., and Altona, C., Tetrahedron 1980, vol. 36, p. 2783.

    Article  CAS  Google Scholar 

  24. Huggins, M.L., J. Am. Chem. Soc., 1953, vol. 75, p. 4123.

    Article  CAS  Google Scholar 

  25. Turyanskaya, A.M., Timofeev, O.S., Kuznetsov, V.V., and Gren’, A.I., Zh. Org. Khim. 1992, vol. 28, p. 79.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ufa State Aviation Technical University, ul. K. Marksa 12, Ufa, Bashkortostan, 450008, Russia

    V. V. Kuznetsov

  2. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062, Russia

    V. V. Kuznetsov & S. A. Bochkor

Authors
  1. V. V. Kuznetsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Bochkor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Kuznetsov.

Additional information

Original Russian Text © V.V. Kuznetsov, S.A. Bochkor, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1805–1810.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kuznetsov, V.V., Bochkor, S.A. Conformational Analysis of 5-Methyl-1,3-oxathiane. Russ J Org Chem 54, 1819–1824 (2018). https://doi.org/10.1134/S107042801812014X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801812014X

Search

Navigation