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Investigation of the possibility of complex formation of bidentate bispidine ligands with copper(ii) salts in solution by proton NMR spectroscopy

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Abstract

The possibility of the complex formation of three bispidines with copper(ii) chloride and acetate in a deuterated DMF solution was studied by NMR titration. For all ligands, the formation of complexes with copper(ii) chloride was clearly detected based on the changes in the signals in the proton NMR spectra. The formation of complexes with copper(ii) acetate was not observed for any of the ligands. The results of the study can be used in the design of metal complex catalysts for the Henry reaction.

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References

  1. X. Bao, X. Li, C. Jiang, W. Xiao, G. Chen, Aust. J. Chem., 2022, 75, 806–819; DOI: https://doi.org/10.1071/CH22136.

    Article  CAS  Google Scholar 

  2. M. R. R. Rénio, F. J. P. M. Sousa, N. C. T. Tavares, A. J. M. Valente, M. E. Silva Serra, D. Murtinho, Appl. Organomet. Chem., 2021, 35, 1–10; DOI: https://doi.org/10.1002/aoc.6175.

    Article  Google Scholar 

  3. B. V. S. Reddy, S. M. Reddy, S. Manisha, C. Madan, Tetrahedron: Asymmetry, 2011, 22, 530–535; DOI: https://doi.org/10.1016/j.tetasy.2011.02.019.

    Article  CAS  Google Scholar 

  4. P. Drabina, E. Horáková, Z. Růžičková, M. Sedlák, Tetrahedron: Asymmetry, 2015, 26, 141–147; DOI: https://doi.org/10.1016/j.tetasy.2015.01.001.

    Article  CAS  Google Scholar 

  5. D. Scharnagel, F. Prause, J. Kaldun, R. G. Haase, M. Breuning, Chem. Commun., 2014, 50, 6623–6625; DOI: https://doi.org/10.1039/C4CC02429J.

    Article  CAS  Google Scholar 

  6. H. Maheswaran, K. L. Prasanth, G. G. Krishna, K. Ravikumar, B. Sridhar, M. L. Kantam, Chem. Commun., 2006, 39, 4066–4068; DOI: https://doi.org/10.1039/B610203D.

    Article  Google Scholar 

  7. S. Zhang, Y. Li, Y. Xu, Z. Wang, Chinese Chem. Lett., 2018, 29, 873–883; DOI: https://doi.org/10.1016/j.cclet.2017.10.001.

    Article  CAS  Google Scholar 

  8. D. Scharnagel, A. Müller, F. Prause, M. Eck, J. Goller, W. Milius, M. Breuning, Chem. — A Eur. J., 2015, 21, 12488–12500; DOI: https://doi.org/10.1002/chem.201502090.

    Article  CAS  Google Scholar 

  9. A. Rossetti, S. Landoni, F. Meneghetti, C. Castellano, M. Mori, G. Colombo Dugoni, A. Sacchetti, New J. Chem., 2018, 42, 12072–12081; DOI: https://doi.org/10.1039/c8nj01930d.

    Article  CAS  Google Scholar 

  10. D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc., 2003, 125, 12692–12693; DOI: https://doi.org/10.1021/ja0373871.

    Article  CAS  PubMed  Google Scholar 

  11. E. S. Mozhaitsev, K. Y. Ponomarev, O. S. Patrusheva, A. V. Medvedko, A. I. Dalinger, A. D. Rogachev, N. I. Komarova, D. V. Korchagina, E. V. Suslov, K. P. Volcho, N. F. Salakhutdinov, S. Z. Vatsadze, Russ. J. Org. Chem., 2020, 56, 1969–1981; DOI: https://doi.org/10.1134/S1070428020110123.

    Article  CAS  Google Scholar 

  12. S. Z. Vatsadze, V. S. Semashko, M. A. Manaenkova, D. P. Krut’ko, V. N. Nuriev, R. D. Rakhimov, D. I. Davlyatshin, A. V. Churakov, J. A. K. Howard, A. L. Maksimov, W. Li, H. Yu, Russ. Chem. Bull., 2014, 63, 895–911; DOI: https://doi.org/10.1007/s11172-014-0526-6.

    Article  CAS  Google Scholar 

  13. M. J. Berardi, W. M. Shih, S. C. Harrison, J. J. Chou, Nature, 2011, 476, 109–113; DOI: https://doi.org/10.1038/nature10257.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. R. M. Almeida, P. Turano, I. Moura, J. J. G. Moura, S. R. Pauleta, ChemBioChem, 2013, 14, 1858–1866; DOI: https://doi.org/10.1002/cbic.201300196.

    Article  CAS  PubMed  Google Scholar 

  15. E. V. Suslov, K. Y. Ponomarev, O. S. Patrusheva, S. O. Kuranov, A. A. Okhina, A. D. Rogachev, A. A. Munkuev, R. V. Ottenbacher, A. I. Dalinger, M. A. Kalinin, S. Z. Vatsadze, K. P. Volcho, N. F. Salakhutdinov, Molecules, 2021, 26, 7539–7558; DOI: https://doi.org/10.3390/molecules26247539.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. D. Shcherbakov, D. Baev, M. Kalinin, A. Dalinger, V. Chirkova, S. Belenkaya, A. Khvostov, D. Krut’ko, A. Medved’ko, E. Volosnikova, E. Sharlaeva, D. Shanshin, T. Tolstikova, O. Yarovaya, R. Maksyutov, N. Salakhutdinov, S. Vatsadze, ACS Med. Chem. Lett., 2022, 13, 140–147; DOI: https://doi.org/10.1021/acsmedchemlett.1c00299.

    Article  CAS  PubMed  Google Scholar 

  17. M. A. Kalinin, S. M. Antropov, A. V. Medvedko, A. O. Gudovannyy, K. A. Lyssenko, S. Z. Vatsadze, Russ. Chem. Bull., 2021, 70, 2247–2251; DOI: https://doi.org/10.1007/s11172-021-3341-x.

    Article  CAS  Google Scholar 

  18. Y.-M. Lee, G. Chung, M.-A. Kwon, S.-N. Choi, Acta Crystallogr. Sect. C. Cryst. Struct. Commun., 2000, 56, 67–68; DOI: https://doi.org/10.1107/S0108270199012160.

    Article  Google Scholar 

  19. B. Jasiewicz, B. Warżajtis, U. Rychlewska, Polyhedron, 2011, 30, 1703–1709; DOI: https://doi.org/10.1016/j.poly.2011.03.043.

    Article  CAS  Google Scholar 

  20. O. I. Levina, K. A. Potekhin, E. N. Kurkutova, Yu. T. Struchkov, O. N. Zefirova, V. A. Palyulin, N. S. Zefirov, Dokl. Akad. Nauk SSSR, 1986, 289, 876–879.

    CAS  Google Scholar 

  21. L. S. Childers, K. Folting, L. L. Merritt, W. E. Streib, Acta Crystallogr. Sect. B. Struct. Crystallogr. Cryst. Chem., 1975, 31, 924–925; DOI: https://doi.org/10.1107/S0567740875004141.

    Article  Google Scholar 

  22. S. Z. Vatsadze, V. K. Bel’skii, S. E. Sosonyuk, N. V. Zyk, N. S. Zefirov, Chem. Heterocycl. Compd., 1997, 33, 300–309; DOI: https://doi.org/10.1007/BF02253110.

    Article  CAS  Google Scholar 

  23. V. A. Palyulin, O. M. Grek, S. V. Emets, K. A. Potekhin, A. E. Lysov, N. S. Zefirov, Dokl. Chem., 2000, 374, 215–217.

    Google Scholar 

  24. V. A. Larionov, L. V. Yashkina, M. G. Medvedev, A. F. Smol’yakov, A. S. Peregudov, A. A. Pavlov, D. B. Eremin, T. F. Savel’yeva, V. I. Maleev, Y. N. Belokon, Inorg. Chem., 2019, 58, 11051–11065; DOI: https://doi.org/10.1021/acs.inorgchem.9b01574.

    Article  CAS  PubMed  Google Scholar 

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Correspondence to S. Z. Vatsadze.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The study was financially supported by the Russian Science Foundation (Project No. 19-73-20090).

We are grateful to the Center for Collective Use of Scientific Equipment of the Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences for help in performing the analysis of the synthesized compounds.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 635–640, March, 2023.

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Pavlov, A.A., Dalinger, A.I., Suslov, E.V. et al. Investigation of the possibility of complex formation of bidentate bispidine ligands with copper(ii) salts in solution by proton NMR spectroscopy. Russ Chem Bull 72, 635–640 (2023). https://doi.org/10.1007/s11172-023-3827-9

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  • DOI: https://doi.org/10.1007/s11172-023-3827-9

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