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Structure and Conformational Analysis of 5-Methyl-2,2-diphenyl-1,3-dioxane

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Abstract

The structure of 5-methyl-2,2-diphenyl-1,3-dioxane has been studied by1H and 13C NMR spectroscopy and X-ray analysis. Its molecules in crystal, as well as in CDCl3 and C6D6 solutions, have achair conformation with equatorial methyl group. The conformational transformation pathways, ΔG0298 value for the 5-methyl group in CDCl3 and C6D6, and the optimal number of solvent molecules in the nearest solvation shell of 5-methyl-2,2-diphenyl-1,3-dioxane have been determined by quantum chemical calculations at the PBE/3ξ and RI-MP2/λ2 levels of theory and by comparing the theoretical and experimental vicinal spin–spin coupling constants.

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REFERENCES

  1. Ram, V.J., Sethi, A., Nath, M., and Pratar, R., The Chemistry of Heterocycles. Chemistry of Six- to Eight-membered N, O, S, P, and Se Heterocycles, Amsterdam: Elsevier, 2019, p. 340. https://doi.org/10.1016/B978-0-12-819210-8.00002-3

  2. Franchini, S., Sorbi, C., Linciano, P., Camevale, G., Tait, A., Ronsisvalle, S., Buccioni, M., Del Bello, F., Cilia, A., Pironal, L., Denora, N., Iacobazzi, R.M., and Brasili, L., Eur. J. Med. Chem., 2019, vol. 176, p. 310. https://doi.org/10.1016/j.ejmech.2019.05.024

    Article  CAS  PubMed  Google Scholar 

  3. Tugarova, A.V., Kazakova, A.N., Kamnev, A.A., and Zlotskij, S.S.,Russ. J. Gen. Chem., 2014, vol. 84, p. 1930. https://doi.org/10.1134/S1070363214100119

    Article  CAS  Google Scholar 

  4. Rakhmankulov, D.L., Karakhanov, R.A., Zlotskii, S.S., Kantor, E.A., Imashev, U.B., and Syrkin, A.M., Itogi Nauki Tekh., Tekhnol. Org. Veshchestv, 1979, no. 5, p. 6.

    Google Scholar 

  5. Kuznetsov, V.V., Chem. Heterocycl. Compd., 2006, vol. 42, p. 559. https://doi.org/10.1007/s10593-006-0127-x

    Article  CAS  Google Scholar 

  6. Kuznetsov, V.V., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 1543. https://doi.org/10.1007/s11172-006-0001-0

    Article  CAS  Google Scholar 

  7. Janssens, J., Risseeuw, M.D.P., Eycken, J.V., and Calenbergh, S.V.,Eur. J. Org. Chem., 2018, vol. 2018, p. 6405. https://doi.org/10.1002/ejoc.201801245

    Article  CAS  Google Scholar 

  8. Cooksey, J., Gunn, A., Philip, J., Kocienski, P.J., Kuhl, A., Uppal, S., Christopher, J.A., and Bell, R., Org. Biomol. Chem., 2004, vol. 2, p. 1719. https://doi.org/10.1039/B400242C

    Article  CAS  PubMed  Google Scholar 

  9. Sinz, C.J. and Rychnovsky, S.D., Top. Curr. Chem., 2001, vol. 216, p. 50. https://doi.org/10.1007/3-540-44726-1_2

    Article  Google Scholar 

  10. Internal Rotation in Molecules, Orville-Thomas, W.J., Ed., London: Wiley, 1974.

  11. Kuznetsov, V.V., Russ. J. Org. Chem., 2014, vol. 50, p. 1227. https://doi.org/10.1134/S1070428014090012

    Article  CAS  Google Scholar 

  12. Laikov, D.N. and Ustynyuk, Yu.A., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 820. https://doi.org/10.1007/s11172-005-0329-x

    Article  CAS  Google Scholar 

  13. Haasnoot, C.A.G., de Leeuw, F.A.A.M., and Altona, C., Tetrahedron, 1980, vol. 36, p. 2783. https://doi.org/10.1016/0040-4020(80)80155-4

    Article  CAS  Google Scholar 

  14. Raskildina, G.Z., Spirikhin, L.V., Zlotskij, S.S., and Kuznetsov, V.V., Russ. J. Org. Chem., 2019, vol. 55, p. 502. https://doi.org/10.1134/S1070428019040146

    Article  CAS  Google Scholar 

  15. Khazhiev, Sh.Yu., Khusainov, M.A., Khalikov, R.A., Kataev, V.A., Tyumkina, T.V., Meshcheryakova, E.S., Khalilov, L.M., and Kuznetsov, V.V.,Russ. J. Org. Chem., 2020, vol. 56, p. 1. https://doi.org/10.1134/S1070428020010017

    Article  CAS  Google Scholar 

  16. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  PubMed  Google Scholar 

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

  18. Huggins, M.L., J. Am. Chem. Soc., 1953, vol. 75, p. 4123. https://doi.org/10.1021/ja01113a001

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The spectral studies of dioxane 1 were carried out at the Agidel joint center (Institute of Petrochemistry and Catalysis, Russian Academy of Sciences).

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Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450062, Ufa, Russia

    A. E. Kuramshina & V. V. Kuznetsov

  2. Bashkir State Medical University, Ministry of Health of the Russian Federation, 450008, Ufa, Russia

    R. A. Khalikov & V. A. Kataev

  3. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 450075, Ufa, Russia

    T. V. Tyumkina, E. S. Meshcheryakova & L. M. Khalilov

  4. Ufa State Aviation Technical University, 450008, Ufa, Russia

    V. V. Kuznetsov

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  1. A. E. Kuramshina
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  2. R. A. Khalikov
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  3. V. A. Kataev
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  4. T. V. Tyumkina
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Correspondence to V. V. Kuznetsov.

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Kuramshina, A.E., Khalikov, R.A., Kataev, V.A. et al. Structure and Conformational Analysis of 5-Methyl-2,2-diphenyl-1,3-dioxane. Russ J Org Chem 56, 1764–1769 (2020). https://doi.org/10.1134/S1070428020100152

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