Synthesis and Study of Mono(arylhydrazino)acenaphthenones and Nickel Complex based on Pyridine-substituted Derivative

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Three mono(arylhydrazino)acenaphthenones, that is, mono(2-pyridylhydrazino)acenaphthenone (Py-mhan, L1), mono(4-cyanophenylhydrazino)acenaphthenone (4-CN-Ph-mhan, L2), and mono(3,4,6-trifluoro-2-pyridylhydrazino)acenaphthenone (FPy-mhan, L3), were synthesized by the reaction of acenaphthene quinone with the appropriate arylhydrazine salt; compounds L2 and L3 were obtained for the first time. The subsequent reaction of L1 with nickel chloride in 2 : 1 ratio led to the octahedral complex [Ni(Py-mhan)2] (I), in which Py-mhan acts as a tridentate ligand. All of the prepared compounds were characterized by elemental analysis, IR and 1H NMR spectroscopy, and cyclic voltammetry; the crystal structures of L3 and I were determined by X-ray diffraction.

Full Text

Restricted Access

About the authors

I. V. Bakaev

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

V. I. Komlyagina

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences; Novosibirsk State National Research University

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk; Novosibirsk

N. F. Romashev

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Author for correspondence.
Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

A. L. Gushchin

Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences

Email: nikolaj.romashev75@gmail.com
Russian Federation, Novosibirsk

References

  1. Wang, J., Soo, H.Sen., and Garcia, F., Commun. Chem., 2020, vol. 3, no. 1, p. 133.
  2. Fomenko, I.S. and Gushchin, A.L., Russ. Chem. Rev., 2020, vol. 89, no. 9, p. 966.
  3. Komlyagina, V.I., Romashev, N.F., Besprozvannykh, V.K., et al., Inorg. Chem., 2023, vol. 62, no. 29, p. 11541.
  4. Romashev, N.F., Mirzaeva, I.V., Bakaev, I.V., et al., J. Struct. Chem., 2022, vol. 63, no. 2, p. 242.
  5. Romashev, NF., Bakaev, I.V., Komlyagina, V.I., et al., J. Struct. Chem., 2022, vol. 63, no. 8, p. 1304.
  6. Fedushkin, I.L., Skatova, A.A., Chudakova, V.A., and Fukin, G.K., Angew. Chem., Int. Ed. Engl., 2003, vol. 42, no. 28, p. 3294.
  7. Fedushkin, I.L., Maslova, O.V., Baranov, E.V., and Shavyrin, A.S., Inorg. Chem., 2009, vol. 48, no. 6, p. 2355.
  8. Bendix, J. and Clark, K.M., Angew. Chem., Int. Ed. Engl., 2016, vol. 55, no. 8, p. 2748.
  9. Bernauer, J., Pölker, J., and Jacobi von Wangelin, A., ChemCatChem, 2022, vol. 14, no. 1, p. e202101182.
  10. Chacon-Teran, M.A. and Findlater, M., Eur. J. Inorg. Chem., 2022, vol. 2022, no. 30, p. e202200363.
  11. Johnson, L.K., Killian, C.M., and Brookhart, M., J. Am. Chem. Soc., 1995, vol. 117, no. 23, p. 641415.
  12. Leatherman, M.D., Svejda, S.A., Johnson, L.K., and Brookhart, M., J. Am. Chem. Soc., 2003, vol. 125, no. 10, p. 3068.
  13. Bridges, C.R., McCormick, T.M., Gibson, G.L., et al., J. Am. Chem. Soc., 2013, vol. 135, no. 35, p. 13212.
  14. Zhai, F. and Jordan, R.F., Organometallics, 2017, vol. 36, no. 15, p. 2784.
  15. Wu, R., Klingler, W., Stieglitz, L., et al., Coord. Chem. Rev., 2023, vol. 474, no. 1, p. 214844.
  16. Fedushkin, I.L., Nikipelov, A.S., Morozov, A.G., et al., Chem.-Eur. J., 2012, vol. 18, no. 1, p. 255.
  17. Yakub, A.M., Moskalev, M.V., Bazyakina, N.L., and Fedushkin, I.L., Russ. Chem. Bull., 2018, vol. 67, no. 3, p. 473.
  18. Arrowsmith, M., Hill, M.S., and Kociok-Kohn, G., Organometallics, 2011, vol. 30, no. 6, p. 1291.
  19. Saini, A., Smith, C.R., Wekesa, F.S., et al., Org. Biomol. Chem., 2018, vol. 16, no. 48, p. 9368.
  20. Tamang, S.R., Cozzolino, A.F., and Findlater, M., Org. Biomol. Chem., 2019, vol. 17, no. 7, p. 1834.
  21. Gushchi, A.L., Romashev, N.F., Shmakova, A.A., et al., Mendeleev Commun., 2020, vol. 30, no. 1, p. 81.
  22. Fomenko, I.S., Gongola, M.I., Shulʹpina, L.S., et al., Catalysts, 2022, vol. 12, no. 10, p. 1168.
  23. Romashev, N.F., Bakae, I.V., Komlyagina, V.I., et al., Int. J. Mol. Sci., 2023, vol. 24, no. 13, p. 10457.
  24. Bakaev, I.V., Romashev, N.F., Komlyagina, V.I., et al., New J. Chem., 2023, vol. 47, no. 40, p. 18825.
  25. Zhou, J.L., Xu, Y.H., Jin, X.X., et al., Inorg. Chem. Commun., 2016, vol. 64, p. 67.
  26. Zhou, J.L., Sun, H.W., Yin, D.H., et al., J. Mol. Struct., 2017, vol. 1134, p. 63.
  27. Gao, Q., Song, Y., Zheng, C., et al., J. Mol. Struct., 2020, vol. 1214, p. 128228.
  28. Su, Y.X., Zhang, C.Z., and Song, M.X., Acta Crystallogr., Sect. C: Struct. Chem., 2017, vol. 73, no. 6, p. 458.
  29. Sheldrick, G.M., Acta Crystallogr., Sect. A: Cryst. Adv., 2015, vol. 71, no. 1, p. 3.
  30. Sheldrick, G.M., Acta Crystallogr., Sect. C: Struct. Chem., 2015, vol. 71, p. 3.
  31. Hubschle, C.B., Sheldrick, G.M., and Dittrich, B., J. Appl. Crystallogr., 2011, vol. 44, no. 6, p. 1281.
  32. Soldatov, D.V., Mendeleev Commun., 1997, vol. 7, no. 3, p. 100.
  33. Bose, N. and Lynton, H., Can. J. Chem., 1973, vol. 51, no. 12, p. 1952.
  34. Zhang, H. and Fang, L., Acta Crystallogr., Sect. E: Struct. Rep. Online, 2005, vol. 61, no. 1, p. m1.
  35. Wriedt, M., Jess, I., and Nather, C., Acta Crystallogr., Sect. E: Struct. Rep. Online, 2010, vol. 66, no. 7, p. m780.
  36. Van Damme, N., Lough, A.J., Gorelsky, S.I., and Lemaire, M.T., Inorg. Chem., 2013, vol. 52, no. 22, p. 13021.
  37. Niklas, J.E., Farnum, B.H., Gorden, J.D., and Gorden, A.E.V., Organometallics, 2017, vol. 36, no. 23, p. 4626.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme 1. Synthesis of compounds L1-L3, I and numbering of protons in compounds L1-L3

Download (198KB)
Indexing metadata
3. Fig. 1. Molecular structure of L3 according to PCA data

Download (58KB)
Indexing metadata
4. Fig. 2. Molecular structure of I according to PCA data

Download (85KB)
Indexing metadata
5. Fig. 3. CBA curves of the L1-L3 compounds in the potential range from -1.6 to 1.7 V (for L1); -1.75 to 1.8 V (for L2); -1.5 to 2.0 V (for L3) (CH2Cl2, SU electrode, c(L1-L3) = 8 × 10-4-2 × 10-3 M, v = 100 mV/s, 0.1 M nBu4NPF6, rt. Ag/AgCl))

Download (130KB)
Indexing metadata
6. Scheme 2. Ar-mhan redox processes

Download (82KB)
Indexing metadata
7. Fig. 4. CVA curves of compound I in the potential range from 0 to -1.7 V and 0 to 2.0 V (CH2Cl2, SU electrode, c(L1-L3) = 1 × 10-3 mol/L, v = 100 mV/s, 0.1 mol/L nBu4NPF6, rt. Ag/AgCl))

Download (78KB)
Indexing metadata

Copyright (c) 2024 Российская академия наук