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Conformational Equilibria of a Thiadiazole Derivative in Solvents of Different Polarities: an NMR Study

  • ON THE 90th ANNIVERSARY OF THE BIRTH OF G.A. KRESTOV
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Abstract

The spatial structure of the 1-[5-(4-methoxyphenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol molecule is analyzed by the methods of nuclear magnetic resonance (NMR) spectroscopy and quantum chemical calculations using the density functional theory. The ratio of probable conformers of the compound in chloroform-d1 and dimethylsulfoxide-d6 is found. Conformational inversion of the compound molecules is observed upon changing the solvent.

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REFERENCES

  1. Y. Li, J. Geng, Y. Liu, et al., ChemMedChem 8, 27 (2013).

    Article  Google Scholar 

  2. Y. Hu, C.-Y. Li, X.-M. Wang, et al., Chem. Rev. Am. Chem. Soc. 114, 5572 (2014).

    Article  CAS  Google Scholar 

  3. B. Sharma, A. Verma, S. Prajapati, and U. K. Sharma, Int. J. Med. Chem. 2013, 1 (2013).

    Google Scholar 

  4. I. A. Khodov, M. Y. Nikiforov, G. A. Alper, et al., J. Mol. Struct. 1035, 358 (2013).

    Article  CAS  Google Scholar 

  5. I. A. Khodov, S. V. Efimov, V. V. Klochkov, et al., Eur. J. Pharm. Sci. 65, 65 (2014).

    Article  CAS  Google Scholar 

  6. G. A. Gamov, I. A. Khodov, K. V. Belov, et al., J. Mol. Liq. 283, 825 (2019).

    Article  CAS  Google Scholar 

  7. K. V. Belov, I. E. Eremeev, V. V. Sobornova, et al., Macroheterocycles 13, 44 (2020).

    Article  CAS  Google Scholar 

  8. I. A. Khodov, K. V. Belov, A. E. Pogonin, et al., J. Mol. Liq. 342, 117372 (2021).

  9. M. Liu, X. A. Mao, C. Ye, et al., J. Magn. Reson. 132, 125 (1998).

    Article  CAS  Google Scholar 

  10. I. A. Khodov, K. V. Belov, S. V. Efimov, and L. A. E. B. de Carvalho, AIP Conf. Proc. 2063 (2019).

  11. H. Kessler, H. Oschkinat, C. Griesinger, and W. Bermel, J. Magn. Reson. 70, 106 (1986).

    CAS  Google Scholar 

  12. J. Stonehouse, P. Adell, A. J. Shaka, and J. Keeler, J. Am. Chem. Soc. 116, 6037 (1994).

    Article  CAS  Google Scholar 

  13. K. Stott, J. Keeler, T. L. Hwang, et al., J. Am. Chem. Soc. 117, 4199 (1995).

    Article  CAS  Google Scholar 

  14. M. J. Thrippleton and J. Keeler, Angew. Chem. Int. Ed. 42, 3938 (2003).

    Article  CAS  Google Scholar 

  15. S. A. Katkova, M. A. Kinzhalov, P. M. Tolstoy, et al., Organometallics 36, 4145 (2017).

    Article  CAS  Google Scholar 

  16. P. P. Kobchikova, S. V. Efimov, I. A. Khodov, and V. V. Klochkov, J. Mol. Liq. 336, 116244 (2021).

  17. S. I. Selivanov, S. Wang, A. S. Filatov, and A. V. Stepakov, Appl. Magn. Reson. 51, 165 (2020).

    Article  CAS  Google Scholar 

  18. S. I. Selivanov, Appl. Magn. Reson. 49, 563 (2018).

    Article  CAS  Google Scholar 

  19. A. S. Smirnov, A. S. Kritchenkov, N. A. Bokach, et al., Inorg. Chem. 54, 11018 (2015).

    Article  CAS  Google Scholar 

  20. I. Khodov, S. Efimov, M. Krestyaninov, et al., J. Pharm. Sci. 110, 1533 (2021).

    Article  CAS  Google Scholar 

  21. K. S. Usachev, A. V. Filippov, B. I. Khairutdinov, et al., J. Mol. Struct. 1076, 518 (2014).

    Article  CAS  Google Scholar 

  22. K. S. Usachev, A. V. Filippov, E. A. Filippova, et al., J. Mol. Struct. 1049, 436 (2013).

    Article  CAS  Google Scholar 

  23. L. F. Galiullina, H. A. Scheidt, D. Huster, et al., Biochim. Biophys. Acta 1861, 584 (2019).

    Article  CAS  Google Scholar 

  24. A. G. Palmer III, J. Cavanagh, P. E. Wright, and M. Rance, J. Magn. Reson. 93, 151 (1991).

    CAS  Google Scholar 

  25. L. E. Kay, P. Keifer, and T. Saarinen, J. Am. Chem. Soc. 114, 10663 (1992).

    Article  CAS  Google Scholar 

  26. J. Schleucher, M. Schwendinger, M. Sattler, et al., J. Biomol. NMR 4, 301 (1994).

    Article  CAS  Google Scholar 

  27. D. O. Cicero, G. Barbato, and R. Bazzo, J. Magn. Reson. 148, 209 (2001).

    Article  CAS  Google Scholar 

  28. A. Bax and D. G. Davis, J. Magn. Reson. 65, 355 (1985).

    CAS  Google Scholar 

  29. I. A. Khodov, M. G. Kiselev, S. V. Efimov, and V. V. Klochkov, J. Magn. Reson. 266, 67 (2016).

    Article  CAS  Google Scholar 

  30. P. A. Kalmykov, I. A. Khodov, V. V. Klochkov, and M. V. Klyuev, Russ. Chem. Bull. 66, 70 (2017).

    Article  CAS  Google Scholar 

  31. G. B. Guseva, E. V. Antina, and M. B. Berezin, ACS Appl. Biol. Mater. 4, 6227 (2021).

    Article  CAS  Google Scholar 

  32. I. A. Khodov, S. V. Efimov, M. Y. Nikiforov, et al., J. Pharm. Sci. 103, 392 (2014).

    Article  CAS  Google Scholar 

  33. A. A. Hoser, D. M. Kamiński, A. Matwijczuk, et al., CrystEngComm 15, 1978 (2013).

    Article  CAS  Google Scholar 

  34. A. A. Hoser, D. M. Kamiński, A. Skrzypek, et al., Cryst. Growth Des. 18, 3851 (2018).

    Article  CAS  Google Scholar 

  35. D. Karcz, A. Matwijczuk, B. Boroń, et al., J. Mol. Struct. 1128, 44 (2017).

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

Our NMR experiments were performed on the equipment of the Krestov Institute of Solution Chemistry, Russian Academy of Sciences (http://www.ckp-rf.ru/usu/503933/).

Funding

This work was supported by the RF Ministry of Higher Education and Science, project nos. 01201260481 and 0120095082; the Russian Foundation for Basic Research, project nos. 18-29-06008 and 20-43-370011; and the RF Presidential Grant Council, project no. МK-662.2021.1.3.

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Authors and Affiliations

  1. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045, Ivanovo, Russia

    I. A. Khodov, K. V. Belov, M. A. Krestyaninov & M. G. Kiselev

Authors
  1. I. A. Khodov
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  2. K. V. Belov
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  3. M. A. Krestyaninov
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  4. M. G. Kiselev
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Correspondence to I. A. Khodov.

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Translated by A. Tulyabaev

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Khodov, I.A., Belov, K.V., Krestyaninov, M.A. et al. Conformational Equilibria of a Thiadiazole Derivative in Solvents of Different Polarities: an NMR Study. Russ. J. Phys. Chem. 96, 765–772 (2022). https://doi.org/10.1134/S0036024422040148

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  • DOI: https://doi.org/10.1134/S0036024422040148

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