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Synthesis and Structure of Dioxomolibdenum(VI) Complexes with Hydrazones of β-Dicarbonyl Compounds. Crystal Structures of Benzoylacetone Nicotinoylhydrazone (H2L1), Acetoacetanilide Benzoylhydrazone (H2L2), and MoO2L1·MeOH Solvate

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Abstract

Two acetylhydrazones, namely benzoylacetone nicotinoylhydrazone (H2L1) and acetoacetanilide benzoylhydrazone (H2L2), and also the MoO2L1·MeOH solvate complex were synthesized and their structure was studied by single crystal X-ray diffraction and IR-spectroscopy methods. Molecules of two hydrazones crystallize in different enehydrazonic tautomeric forms: hydrazonic for H2L1 and enehydrazine-α-oxyazine for H2L2. In the both organic molecules, two planar six-membered aromatic cycles are connected by zigzag six- and seven-membered C–C–C–N–N(H)­–C– and –N–C–C–C–C–N–N–C– chains, respectively. The both organic molecules are stabilized by N–H···O intermolecular hydrogen bonds (and also by N–H···O intramolecular hydrogen bond in the H2L2 structure). In the MoO2L1·MeOH solvate, the molybdenum atom has an octahedral coordination environment formed by two cis-O2(oxo) and tridentate (ONO)bis(chelate) (L2)2– ligands, and also a methanol molecule. Atoms N(L1) and O(MeOH) are in trans-position to O(oxo); two atoms O(L1)—in cis-position to O(oxo) and trans-position to each other.

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REFERENCES

  1. Abdu, A.M., Al-Fakeh, M.S., Alhagri, I.A., Alhakimi, A.N., Saeed, S.E.-S., Shakdofa, A.M.E., and Shakdofa, M.M.E., J. Korean Chem. Soc., 2021, vol. 65, no. 2, p. 93. https://doi.org/10.5012/jkcs.2021.65.2.93

    Article  CAS  Google Scholar 

  2. Busch, R., Carter, A.B., Konidaris, K.F., Kühne, I.A., González, R., Anson, Ch.E., and Powell, A.K., Chem. Eur. J., 2020, vol. 26, no. 51, p. 11835. https://doi.org/10.1002/chem.202001668

    Article  CAS  PubMed  Google Scholar 

  3. Kuriakose, D. and Kurup, M.R.P., Polyhedron, 2019, vol. 170, p. 749. https://doi.org/10.1016/j.poly.2019.06.041

    Article  CAS  Google Scholar 

  4. Liang, M. and Zou, D.-H., Inorg. Nano-Met. Chem., 2017, vol. 47, no. 1, p. 110. https://doi.org/10.1080/15533174.2016.1149730

    Article  CAS  Google Scholar 

  5. Majumder, S., Pasayat, S., Roy, S., Dash, S.P., Dhaka, S., Maurya, M.R., Reichelt, M., Reuter, H., Brzezinski, K., and Dinda, R., Inorg. Chim. Acta, 2018, vol. 469, p. 366. https://doi.org/10.1016/j.ica.2017.09.043

    Article  CAS  Google Scholar 

  6. Kargar, H., Fallah-Mehrjardi, M., Behjatmanesh-Ardakani, R., Munawar, K.S., Ashfaq, M., and Tahir, M.N., Trans. Met. Chem., 2021, vol. 46, no. 6, p. 437. https://doi.org/10.1007/s11243-021-00460-w

    Article  CAS  Google Scholar 

  7. Gamov, G.A. and Zavalishin, M.N., Russ. J. Inorg. Chem., 2021, vol. 66, no. 10, p. 1561. https://doi.org/10.1134/S0036023621100053

    Article  CAS  Google Scholar 

  8. Zavalishin, M.N., Gamov, G.A., Khokhlova, A.Yu., Gashnikova, A.V., and Sharnin, V.A., Russ. J. Inorg. Chem., 2020, vol. 65, no. 1, p. 119. https://doi.org/10.1134/S0036023620010209

    Article  CAS  Google Scholar 

  9. Sang, Y.-L., Zhang, X.-H., Lin, X.-S., Liu, Y.-H., and Liu, X.-Y., J. Coord. Chem., 2020, vol. 73, no. 1, p. 164. https://doi.org/10.1080/00958972.2019.1707192

    Article  CAS  Google Scholar 

  10. Cvijanović, D., Pisk, J., Pavlović, G., Šišak-Jung, D., Matković-Calogović, D., Cindrić, M., Agustin, D., and Vrdoljak, V., New J. Chem., 2019, vol. 43, no. 4, p. 1791. https://doi.org/10.1039/c8nj04074e

    Article  CAS  Google Scholar 

  11. Pisk, J., Rubčić, M., Kuzman, D., Cindrić, M., Agustin, D., and Vrdoljak, V., New J. Chem., 2019, vol. 43, no. 14, p. 5531. https://doi.org/10.1039/c9nj00229d

    Article  CAS  Google Scholar 

  12. Mohan, B., Choudhary, M., Bharti, S., Jana, A., Das, N., Muhammad, S., Al-Sehemi, A.G., and Kumar, S., J. Mol. Struct., 2019, vol. 1190, p. 54. https://doi.org/10.1016/j.molstruc.2019.04.05

    Article  CAS  Google Scholar 

  13. Sahani, A.J., Jayaram, R.V., and Burange, A.S., Mol. Сatal., 2018, vol. 450, p. 14. https://doi.org/10.1016/j.mcat.2018.02.028

    Article  CAS  Google Scholar 

  14. Lakma, A., Hossain, S. M., Van Leusen, J., Kögerler, P., and Singh, A. K., Dalton Trans., 2019, vol. 48, no. 22, p. 7766. https://doi.org/10.1039/c9dt01041f

    Article  CAS  PubMed  Google Scholar 

  15. Hossain, S.M., Lakma, A., Pradhan, R.N., Demeshko, S., and Singh, A.K., Dalton Trans., 2017, vol. 46, no. 37, p. 12612. https://doi.org/10.1039/c7dt02433a

    Article  CAS  PubMed  Google Scholar 

  16. Maurya, M.R., Tomar, R., Rana, L., and Avecilla, F., Eur. J. Inorg. Chem., 2018, vol. 2018, no. 25, p. 2952. https://doi.org/10.1002/ejic.201800440

    Article  CAS  Google Scholar 

  17. Maurya, M.R., Dhaka, S., and Avecilla, F., Polyhedron, 2015, vol. 96, p. 79. https://doi.org/10.1016/j.poly.2015.05.001

    Article  CAS  Google Scholar 

  18. Moradi-Shoeili, Z., Boghae, D.M., Amini, M., Bagherzadeh, M., and Notas, B., Inorg. Chem. Commun., 2013, vol. 27, p. 26. https://doi.org/10.1016/j.inoche.2012.10.016

    Article  CAS  Google Scholar 

  19. Pasayat, S., Dash, S.P., Roy, S., Dinda, R., Dhaka, S., Maurya, M.R., Kaminsky, W., Patil, Y.P., and Nethaji, М., Polyhedron, 2014, vol. 67, p. 1. https://doi.org/10.1016/j.poly.2013.08.055

    Article  CAS  Google Scholar 

  20. Kurbah, S.D., Kumar, A., Syiemlieh, I., Asthana, M., and Lal, R.A., Inorg. Chem. Commun., 2017, vol. 86, p. 1. https://doi.org/10.1016/j.inoche.2017.09.016

    Article  CAS  Google Scholar 

  21. Maurya, M.R., Rana, L., and Avecilla, F., Polyhedron, 2017, vol. 126, p. 60. https://doi.org/10.1016/j.poly.2017.01.006

    Article  CAS  Google Scholar 

  22. Hu, X.-M., Xue, L.-W., Zhang, C.-X., and Zhao, G.-Q., Synth. React. Inorg. Met.-Org, Nano-Met. Chem., 2014, vol. 44, p. 713. https://doi.org/10.1080/15533174.2013.790435

    Article  CAS  Google Scholar 

  23. Jaiswal, V., Gupta, S.R., Rastogi, R.B., Kumar, R., and Singh, V.P., J. Mater. Chem. A, 2015, vol. 3, no. 9, p. 5092. https://doi.org/10.1039/c4ta05663a

    Article  CAS  Google Scholar 

  24. Rastogi, R.B., Maurya, J.L., and Jaiswal, V., Tribol. Trans., 2013, no. 56, p. 592. https://doi.org/10.1080/10402004.2012.748115

    Article  CAS  Google Scholar 

  25. Pisk, J., Bilić, L., Đaković, M., Cvijanović, D., Damjanović, V., Lovrić, J., Rubčić, M., Vrdoljak, V., and Cindrić, M., Polyhedron, 2018, vol. 145, p. 70. https://doi.org/10.1016/j.poly.2018.02.003

    Article  CAS  Google Scholar 

  26. Cordas, C.M. and Moura, J.J.G., Coord. Chem. Rev., 2019, vol. 394, p. 53. https://doi.org/10.1016/j.ccr.2019.05.005

    Article  CAS  Google Scholar 

  27. Asha, T.M. and Kurup, M.R.P., Polyhedron, 2019, vol. 169, p. 151. https://doi.org/10.1016/j.poly.2019.04.045

    Article  CAS  Google Scholar 

  28. Yusupov, V.G., Nasirdinov, S.D., Yakimovich, S.I., and Parpiev, N.Ya., Koord. Khim., 1984, vol. 10, no. 3, p. 387.

    CAS  Google Scholar 

  29. Kraudelt, H., Ludwig, E., Schilde, U., and Uhlemann, E., Z. Naturforsch., 1995, vol. 51b, p. 95.

    Article  Google Scholar 

  30. Kargar, H., Kia, R., Froozandeh, F., Sadr, M.H., and Tahir, M.N., Acta Cryst. E, 2011, vol. 67, p. o209. https://doi.org/10.1107/S160053681005275X

  31. Kargar, H., Kia, R., Moghadamm, M., and Tahir, M.N., Acta Cryst. E, 2011, vol. 67, p. o367. https://doi.org/10.1107/S1600536811000948

  32. Paciorek, P., Szklarzewicz, J., Trzewik, B., Cież, D., Nitek, W., Hodorowicz, M., and Jurowska, A., J. Org. Chem., 2021, vol. 86, p. 1649. https://doi.org/10.1021/acs.joc.0c02451

    Article  CAS  PubMed  Google Scholar 

  33. Abramenko, V.L. and Sergienko, V.S., Russ. J. Inorg. Chem., 2009, vol. 54, no. 13, p. 2031. https://doi.org/10.1134/S0036028691.30014

    Article  Google Scholar 

  34. Vrdoljak, V., Mandarić, M., Hrenar, T., Đilović, I., Pisk, J., Pavlović, G., Сindrić, M., and Agustin, D., Cryst. Growth Design, 2019, vol. 19, p. 3000. https://doi.org/10.1021/acs.cgd.9b00231

    Article  CAS  Google Scholar 

  35. Sergienko, V.S., Abramenko, V.L., Churakov, A.V., Surazhskaya, M.D., Russ. J. Inorg. Chem., 2021, vol. 66, no. 12, p. 1854. https://doi.org/10.1134/S0036023621120159

    Article  CAS  Google Scholar 

  36. Nandy, M., Shit, S., Rizzoli, C., Pilet, G., and Mitra, S., Polyhedron., 2015, vol. 88, p.63. https://doi.org/10.1016/j.poly.2014.12.017

    Article  CAS  Google Scholar 

  37. Banße, W., Ludwig, E., Shilde, U., Uhlemann, E., Weller, F., and Lehmann, A., Z. Anorg. Allg. Chem., 1995, vol. 621, no. 7, p. 1275. https://doi.org/10.1002/zaac.19956210730

    Article  Google Scholar 

  38. Sergienko, V.S., Abramenko, V.L., Minacheva, L.H., Porai-Koshits, M.A., and Saharova, V.G., Koord. Khim., 1993, vol.19, no. 1, p. 28.

    CAS  Google Scholar 

  39. Kargar, H., Porootan, P., Fallah-Mehrjardi, M., Behjatmanesh-Ardakani, R., Rudbayi, H.A., Munawar, K.S., Ashfaq, M., and Tahir, M.N., Inorg. Chim. Acta, 2021, vol. 523, p. 120414. https://doi.org/10.1016/j.ica.2021.120414

    Article  CAS  Google Scholar 

  40. Sheldrick, G.M., SADABS, Program for Scaling and Correction of Area detector Data, University of Göttingen. Germany, 1997.

  41. Sheldrick, G.M., Acta. Cryst. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

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The work was carried out within the framework of the state assignment of the N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences in the field of fundamental scientific research.

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Authors and Affiliations

  1. N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, 119991, Moscow, Russia

    V. S. Sergienko, A. V. Churakov & M. D. Surashskaya

  2. V. Dahl Lugansk State University, 91034, Lugansk, Ukraine

    V. L. Abramenko

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  1. V. S. Sergienko
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  3. A. V. Churakov
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Correspondence to V. L. Abramenko.

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Sergienko, V.S., Abramenko, V.L., Churakov, A.V. et al. Synthesis and Structure of Dioxomolibdenum(VI) Complexes with Hydrazones of β-Dicarbonyl Compounds. Crystal Structures of Benzoylacetone Nicotinoylhydrazone (H2L1), Acetoacetanilide Benzoylhydrazone (H2L2), and MoO2L1·MeOH Solvate. Russ J Gen Chem 92, 1032–1039 (2022). https://doi.org/10.1134/S1070363222060147

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