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New Oxymederivatives of Perfluorinated 1,3-Diketone: Synthesis, Properties, Studies by DFT and TD-DFT Methods

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Abstract

A number of hitherto unknown trifluorinated beta-diketone oxymes were obtained by direct nitrosation with sodium nitrite in an acidic medium. 4,4,4-Trifluoro-2-(hydroxyimino)-1-(thiophene-2-yl)butane-1,3-dione and 4,4,4-trifluoro-2-(hydroxyimino)-1-phenylbutane-1,3-dione have been characterized by various physicochemical methods. The structure of the formed compounds was confirmed using FTIR, UV-visible spectroscopy, NMR and GC-MS. The spectral characteristics of the obtained compounds were modeled using DFT and TD-DFT calculations.

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REFERENCES

  1. Song, L. and Zhu, S., J. Fluor. Chem., 2001, vol. 111, p. 201. https://doi.org/10.1016/S0022-1139(01)00454-7

    Article  CAS  Google Scholar 

  2. Qing, F., Liu, X., Ma, J., Shen, Q., Song, Q., and Tang, P., CCS Chem., 2022, vol. 4, p. 2518. https://doi.org/10.31635/ccschem.022.202201935

    Article  CAS  Google Scholar 

  3. Barkley, L.B. and Levine, R., J. Am. Chem. Soc., 1951, vol. 73, p. 4625. https://doi.org/10.1021/ja01154a037

    Article  CAS  Google Scholar 

  4. Liu, Y., Guo, J., Zhang, H., and Wang, Y., Angew. Chem. Int. Ed., 2002, vol. 41, p. 182.

    Article  CAS  Google Scholar 

  5. Ono, K., Yoshikawa, K., Tsuji, Y., Yamaguchi, H., Uozumi, R., Tomura, M., Tagaa, K., and Saito, K., Tetrahedron, 2007, vol. 63, p. 9354. https://doi.org/10.1016/j.tet.2007.07.004

    Article  CAS  Google Scholar 

  6. Rickerby, J. and Steinke, J.H.G., Chem. Rev., 2002, vol. 102, p. 1525. https://doi.org/10.1021/cr0104476

    Article  CAS  PubMed  Google Scholar 

  7. Yonetoku, Y., Kubota, H., Okamoto, Y., Ishikawa, J., Takeuchi, M., Ohta, M., and Tsukamoto, S., Bioorg. Med. Chem., 2006, vol. 14, p. 5370. https://doi.org/10.1016/j.bmc.2006.03.039

    Article  CAS  PubMed  Google Scholar 

  8. Wang, D., Fan, L., Zheng, C., and Fang, Z., J. Fluor. Chem., 2010, vol. 131, p. 584. https://doi.org/10.1016/j.jfluchem.2010.01.005

    Article  CAS  Google Scholar 

  9. Christian, K., Fourie, E., Conradie, J., and Swarts, J.C., Organometallics, 2008, vol. 27, p. 353. https://doi.org/10.1021/om700609z

    Article  CAS  Google Scholar 

  10. Hansen, P.E., Pharmaceuticals (Basel), 2021, vol. 14, p. 1189. https://doi.org/10.3390/ph14111189

    Article  CAS  PubMed  Google Scholar 

  11. Tsukerman, S.V., Nikitchenko, V.M., and Rozum, Y.S. Chem. Heterocycl. Compd., 1967, vol. 3, p. 361. https://doi.org/10.1007/BF00945365

    Article  Google Scholar 

  12. Dunning, T.H. Jr., J. Chem. Phys., 1989, vol. 90, p. 1007. https://doi.org/10.1063/1.456153

    Article  CAS  Google Scholar 

  13. Grimme, S., Antony, J., Ehrlich, S., and Krieg, H., J. Chem. Phys., 2010, vol. 132, p. 154104. https://doi.org/10.1063/1.3382344

    Article  CAS  PubMed  Google Scholar 

  14. Weigend, F. and Ahlrich, R., Phys. Chem. Chem. Phys., 2005, vol. 7, p. 3297. https://doi.org/10.1039/b508541a

    Article  CAS  PubMed  Google Scholar 

  15. Lutoshkin, M.A. and Kazachenko, A.S., J. Comput. Methods Sci. Eng., 2017, vol. 17, p. 851. https://doi.org/10.3233/JCM-170745

    Article  CAS  Google Scholar 

  16. Schmidt, M.W., Comput. Chem., 1993, vol. 14, p. 1347. https://doi.org/10.1002/jcc.540141112

    Article  CAS  Google Scholar 

  17. Adamo, C. and Barone, V., J. Chem. Phys., 1999, vol. 110, p. 6158. https://doi.org/10.1063/1.478522

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

This work was conducted within the framework of the budget project FWES-2021-0012 for Institute of Chemistry and Chemical Technology SB RAS using the equipment of Krasnoyarsk Regional Research Equipment Centre of SB RAS. Numerical computations were performed on the MVS-1000M cluster of the Institute of computational modeling SB RAS.

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Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”, 660036, Krasnoyarsk, Russia

    D. S. Volkova, T. Y. Ivanenko & M. A. Lutoshkin

  2. Siberian Federal University, 660041, Krasnoyarsk, Russia

    A. V. Oberenko

  3. Reshetnev Siberian State University of Science and Technology, 660037, Krasnoyarsk, Russia

    A. A. Kukushkin & E. V. Root

  4. Krasnoyarsk State Medical University named after Professor V.F. Voyno-Yasenetsky, 660022, Krasnoyarsk, Russia

    E. V. Root

  5. Criminal Expertise Centre of Directorate for Law Enforcement in Transport Means of Russian Ministry of Internal Affairs for Siberian Federal District, 660058, Krasnoyarsk, Russia

    A. V. Oberenko

Authors
  1. D. S. Volkova
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  2. T. Y. Ivanenko
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  3. A. A. Kukushkin
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  4. E. V. Root
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  5. A. V. Oberenko
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  6. M. A. Lutoshkin
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Correspondence to D. S. Volkova.

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Volkova, D.S., Ivanenko, T.Y., Kukushkin, A.A. et al. New Oxymederivatives of Perfluorinated 1,3-Diketone: Synthesis, Properties, Studies by DFT and TD-DFT Methods. Russ J Org Chem 59, 1363–1369 (2023). https://doi.org/10.1134/S1070428023080110

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