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Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane

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Abstract

The structure of 5,5-bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane, a promising reagent for fine organic synthesis and a potential bactericidal compound, was investigated by 1Н and 13С NMR spectroscopy and X-ray structural analysis. Both in the crystalline state and in solution, molecules of this compound have a chair conformation with an equatorial orientation of the aromatic substituent. Density functional theory calculations at the PBE/3ξ level of theory were used to determine the pathway of conformational transformations and the potential barriers for internal rotation of aromatic and N(CH3)2 groups both for the isolated molecule and for a chloroform solution. A conclusion was drawn that the nearest solvation shell of the studied 1,3-dioxane comprises a relatively small (up to four) number of solvent molecules.

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REFERENCES

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

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

    Article  CAS  Google Scholar 

  3. Rakhmankulov, D.L., Karakhanov, R.A., Zlotskii, S.S., Kantor, E.A., Imashev, U.B., and Syrkin, A.M., Itogi Nauki Tekh., Ser. Tekhnol. Org. Veshchestv, 1979, p. 6.

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

    Article  CAS  Google Scholar 

  5. 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 

  6. 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 

  7. 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 

  8. 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 

  9. 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 

  10. 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 

  11. Kurmaeva, E.S., Chalova, O.B., Chistoedova, G.I., Lapuka, L.F., Kiladze, T.K., Kantor, E.A., and Rakhmankulov, D.L., Zh. Org. Khim., 1985, vol. 21, p. 131.

    CAS  Google Scholar 

  12. Bochkor, S.A., Lapuka, L.F., Kurmaeva, E.S., Chalova, O.B., Zlotskii, S.S., and Rakhmankulov, D.L., Chem. Heterocycl. Compd., 1987, vol. 23, p. 500. https://doi.org/10.1007/BF00476374

    Article  Google Scholar 

  13. Khazhiev, Sh.Yu., Khusainov, M.A., and Kantor, E.A., Russ. J. Gen. Chem., 2011, vol. 81, p. 153. https://doi.org/10.1134/S1070363211010282

    Article  CAS  Google Scholar 

  14. 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 

  15. Khazhiev, Sh.Yu., Khusainov, M.A., Khalikov, R.A., Tyumkina, T.V., Meshcheryakova, E.S., Khalilov, L.M., and Kuznetsov, V.V., Russ. J. Org. Chem., 2018, vol. 54, p. 1076. https://doi.org/10.1134/S1070428018070175

    Article  CAS  Google Scholar 

  16. Khazhiev, Sh.Yu., Khusainov, M.A., Khalikov, R.A., Tyumkina, T.V., Meshcheryakova, E.S., Khalilov, L.M., and Kuznetsov, V.V., Russ. J. Gen. Chem., 2018, vol. 88, p. 397. https://doi.org/10.1134/S1070363218030040

    Article  CAS  Google Scholar 

  17. Khazhiev, Sh.Yu., Khusainov, M.A., Khalikov, R.A., Tyumkina, T.V., Meshcheryakova, E.S., Khalilov, L.M., and Kuznetsov, V.V., Russ. J. Gen. Chem., 2019, vol. 89, p. 199. https://doi.org/10.1134/S0044460X19020057

    Article  CAS  Google Scholar 

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

  19. Khazhiev, Sh.Yu., Khusainov, M.A., and Kantor, E.A., Russ. J. Org. Chem., 2011, vol. 47, p. 450. https://doi.org/10.1134/S1070428011030225

    Article  CAS  Google Scholar 

  20. Mackenzie, R.K. and MacNicol, D.D., J. Chem. Soc. D, 1970, p. 1299. https://doi.org/10.1039/C29700001299

  21. Novikov, V.P., Samdal, S., and Vilkov, L.V., Russ. J. Gen. Chem., 2004, vol. 74, p. 1247. https://doi.org/10.1007/s11176-005-0146-9

    Article  CAS  Google Scholar 

  22. 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 

  23. Kuznetsov, V.V., Russ. J. Struct. Chem., 2018, vol. 59, p. 1374. https://doi.org/10.1134/S0022476618060173

    Article  CAS  Google Scholar 

  24. Valiakhmetova, O.Yu. and Kuznetsov, V.V., Russ. J. Org. Chem., 2021, vol. 57, p. 20. https://doi.org/10.1134/S1070428021010036

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

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ACKNOWLEDGMENTS

The structural study of dioxane 1 was performed at the Agidel Center for Collective Use, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences.

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Authors and Affiliations

  1. Bashneft Public Corporation, 450077, Ufa, Russia

    Sh. Yu. Khazhiev

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

    M. A. Khusainov & V. V. Kuznetsov

  3. Bashkir State Medical University, 450008, Ufa, Russia

    R. A. Khalikov & V. A. Kataev

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

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

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

    V. V. Kuznetsov

Authors
  1. Sh. Yu. Khazhiev
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  2. M. A. Khusainov
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  3. R. A. Khalikov
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  4. V. A. Kataev
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  5. T. V. Tyumkina
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  6. E. S. Meshcheryakova
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  7. L. M. Khalilov
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  8. V. V. Kuznetsov
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Correspondence to V. V. Kuznetsov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1146–1153 https://doi.org/10.31857/S051474922108005X.

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Khazhiev, S.Y., Khusainov, M.A., Khalikov, R.A. et al. Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2-[4-(dimethylamino)phenyl]-1,3-dioxane. Russ J Org Chem 57, 1268–1274 (2021). https://doi.org/10.1134/S1070428021080054

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