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Conformational analysis of 2-methyl-5-nitro-1,3,2-dioxaborinane

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Abstract

Quantum-chemical methods HF/6-31G(d), HF/6-31+G(d), MP2/6-31G(d)//HF/6-31G(d), and MP2/6-31+G(d)//HF/6-31+G(d) were used to investigate the conformational isomerization of 2-methyl-5-nitro-1,3,2-dioxaborinane. It has been shown that a potential energy surface of this compound includes two minima: an axial form of semi-chair and equatorial sofa together with a transition state belonging to the conformation of 2,5-twist-form. A comparison between experimental NMR 1H and theoretical vicinal coupling constants was used to determine the quantitative conformational composition of cyclic boric acid ester and a value of ΔG 0 for nitro group at the ring carbon atom C5 in CCl4 and C6D5NO2 solutions.

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References

  1. Gren’, A.I. and Kuznetsov, V.V., Khimiya tsiklicheskikh efirov bornykh kislot (Chemistry of Cyclic Esters of Boric Acids), Kiev: Naukova Dumka, 1988.

    Google Scholar 

  2. Rossi, K. and Pihlaya, K., Acta Chem. Scand. B, 1985, vol. 39, no. 8, p. 671.

    Article  Google Scholar 

  3. Matteson, D.S., J. Organometal. Chem., 1999, vol. 581, no. 1, p. 51.

    Article  CAS  Google Scholar 

  4. Kuznetsov, V.V., Zh. Obshch. Khim., 2000, vol. 70, no. 1, p. 71.

    Google Scholar 

  5. Kuznetsov, V.V., Doctoral Sci. Dissertation, Ufa, 2002.

  6. Kliegel, W., Preu, L., Rettig, S.J., and Trotter, J., Can. J. Chem., 1986, vol. 64, no. 9, p. 1855.

    Article  CAS  Google Scholar 

  7. Kuznetsov, V.V., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, no. 7, p. 1499.

  8. Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Zh. Org. Khim., 2008, vol. 44, no. 5, p. 783.

    Google Scholar 

  9. Kuznetsov, V.V., Uspekhi organicheskogo kataliza i khimii geterotsiklov (Advanced Organic Catalysis and Heterocycle Chemistry), Moscow: Khimiya, 2006, p. 336.

    Google Scholar 

  10. Kuznetsov, V.V., Zakharov, K.S., Petrovskii, I.V., and Gren’, A.I., Khim. Geterotsikl. Soed., 1990, no. 8, p. 1107.

  11. Kuznetsov, V.V., Novikov, A.N., Rublev, I.S., and Markolenko, P.Yu., Khim. Geterotsikl. Soed., 2003, no. 3, p. 426.

  12. Kuznetsov, V.V., Valiakhmetova, O.Yu., and Bochkor, S.A., Khim. Geterotsikl. Soed., 2007, no. 12, p. 1860.

  13. Urbanski, T., J. Sci. Int. Res., 1974, vol. 33, p. 124.

    CAS  Google Scholar 

  14. Kliegel, W., Preu, L., Rettig, S.J., and Trotter, J., Can. J. Chem., 1985, vol. 63, no. 2, p. 509.

    Article  CAS  Google Scholar 

  15. Kuznetsov, V.V. and Bochkor, S.A., Khim. Geterotsikl. Soed., 1999, no. 8, p. 1065.

  16. Valiakhmetova, O.Yu., Bochkor, S.A., and Kuznetsov, V.V., Khim. Geterotsikl. Soed., 2008, no. 10, p. 1593.

  17. HyperChem 7.01. Trial version. www.hyper.com.

  18. Jensen, F.R., Bushweller, C.H., and Beck, B.H., J. Am. Chem. Soc., 1969, vol. 91, no. 2, p. 344.

    Article  CAS  Google Scholar 

  19. Vnutrenneye vrashcheniye molekul (Internal Rotation of Molecules), Orvill-Tomas, W.J., Ed., Moscow: Mir, 1975, p. 355.

    Google Scholar 

  20. Kaloustian, M.K., Dennis, N., Mager, S., Evans, S.A., Alcudia, F., and Eliel, E.L., J. Am. Chem. Soc., 1976, vol. 98, no. 4, p. 956.

    Article  CAS  Google Scholar 

  21. Eliel, E., Angew. Chem., 1972, vol. 84, no. 17, p. 779.

    Article  Google Scholar 

  22. Anteunis, M.J.O., Tavernier, D., and Borremans, F., Heterocycles, 1976, vol. 4, no. 2, p. 293.

    Article  CAS  Google Scholar 

  23. Durig, J.R., Smooter Smith, J.A., Li, Y.S., and Wasacz, F.M., J. Mol. Struct., 1983, vol. 99, p. 45.

    Article  CAS  Google Scholar 

  24. Zefirov, N.S., Blagoveshchenskii, V.S., Kazimirchik, I.V., and Yakovleva, O.P., Zh. Org. Khim., 1971, vol. 7, no. 3, p. 594.

    CAS  Google Scholar 

  25. Haasnoot, C.A.G., de Leeuw, F.A.A.M., and Altona, C., Tetrahedron, 1980, vol. 36, no. 19, p. 2783.

    Article  CAS  Google Scholar 

  26. Kuznetsov, V.V., Dep. VINITI, Moscow, 1983, no. 5646-83.

  27. Huggins, M.L., J. Am. Chem. Soc., 1953, vol. 75, no. 17, p. 4123.

    Article  CAS  Google Scholar 

  28. Carey, F. and Sundberg, R., Advanced Organic Chemistry, New York, 1981, vol. 1, p. 21.

    Google Scholar 

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Authors and Affiliations

  1. Ufa State Oil Technical University, ul. Kosmonavtov 1, Ufa, 450062, Russia

    O. Yu. Valiakhmetova, S. A. Bochkor & V. V. Kuznetsov

  2. Institute of Molecular and Crystal Physics of Ufa Scientific Centre, Russian Academy of Sciences, pr. Octyabrya 151, Ufa, 450075, Russia

    V. V. Kuznetsov

Authors
  1. O. Yu. Valiakhmetova
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  2. S. A. Bochkor
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  3. V. V. Kuznetsov
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Correspondence to V. V. Kuznetsov.

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Original Russian Text © O.Yu. Valiakhmetova, S.A. Bochkor, V.V. Kuznetsov, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 4, pp. 576–580.

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Valiakhmetova, O.Y., Bochkor, S.A. & Kuznetsov, V.V. Conformational analysis of 2-methyl-5-nitro-1,3,2-dioxaborinane. Russ J Gen Chem 80, 737–741 (2010). https://doi.org/10.1134/S1070363210040092

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  • DOI: https://doi.org/10.1134/S1070363210040092

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