chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2025-20-1-47-54KJJVQAchemicallytech-2218Research ArticleCHEMISTRY AND TECHNOLOGY OF INORGANIC MATERIALSХИМИЯ И ТЕХНОЛОГИЯ НЕОРГАНИЧЕСКИХ МАТЕРИАЛОВSynthesis and characterization of rare earth metal complexes with novel Schiff baseСинтез и характеристика комплексов металлов редкоземельных элементов на новом основании Шиффаhttps://orcid.org/0000-0003-0553-8873АббасоваГ. Г.AbbasovaG. G.

Аббасова Гюлю Ганимат, к.х.н.

АZ 1143, Баку, пр-т Гусейна Джавида, 113

Scopus Author ID 57836278800

Gulu G. Abbasova, PhD

Scopus Author ID 57836278800

113, H. Javid Avenue, Baku, АZ 1143

veliyeva_g23@yahoo.comhttps://orcid.org/0000-0002-1766-5450МеджидовА. А.MedjidovA. A.

Меджидов Аждар Акпер, Академик Национальной академии наук Азербайджана, д.х.н.

АZ 1143, Баку, пр-т Гусейна Джавида, 113

Scopus Author ID 57208439465

Ajdar A. Medjidov, Academician at the Azerbaijan National Academy of Sciences, Dr. Sci. (Chem.)

Scopus Author ID 57208439465

113, H. Javid Avenue, Baku, АZ 1143

ajdarmedjidov@gmail.comИсмаиловР. Х.IsmayilovR. H.

Исмаилов Раййат Гусейн, д.х.н.

АZ 1143, Баку, пр-т Гусейна Джавида, 113

Scopus Author ID 12799990200

Rayyat H. Ismayilov, Dr. Sci.

Scopus Author ID 12799990200

113, H. Javid Avenue, Baku, АZ 1143

ismayilov.rayyat@gmail.comhttps://orcid.org/0000-0002-5923-0420ПашаджановА. М.PashajanovA. M.

Пашаджанов Айдын Магомед, к.х.н.

АZ 1143, Баку, пр-т Гусейна Джавида, 113

Scopus Author ID 57373936700

Aydin M. Pashajanov, PhD

Scopus Author ID 57373936700

113, H. Javid Avenue, Baku, АZ 1143

aydin.pashajanov@gmail.comhttps://orcid.org/0000-0002-2702-7321ФатуллаеваП. А.FatullayevaP. A.

Фатуллаева Перизат Амрулла, д.х.н.

АZ 1143, Баку, пр-т Гусейна Джавида, 113

Scopus Author ID 17134702200

Perizad A. Fatullayeva, Dr. Sci.

Scopus Author ID 17134702200

113, H. Javid Avenue, Baku, АZ 1143

pfatullayeva@gmail.comМинистерство науки и образования Азербайджанской республики, Институт катализа и неорганической химии имени академика М. НагиеваАзербайджанMinistry of Science and Education of the Republic of Azerbaijan, Academician M. Nagiyev Institute of Catalysis and Inorganic ChemistryAzerbaijan2025050320252014754Copyright © Abbasova G.G., Medjidov A.A., Ismayilov R.H., Pashajanov A.M., Fatullayeva P.A., 20252025Аббасова Г.Г., Меджидов А.А., Исмаилов Р.Х., Пашаджанов А.М., Фатуллаева П.А.Abbasova G.G., Medjidov A.A., Ismayilov R.H., Pashajanov A.M., Fatullayeva P.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/2218Objectives

Objectives. The work set out to synthesize Schiff base ligands containing a hydrazone moiety of (Z)-2-((E)-1-hydroxyethylidene)hydrazineylidene)-2-phenylacetic acid, as well as their praseodymium, samarium, europium, and gadolinium complexes, and to study their structure.

Methods

Methods. The structure of ligands was identified by infrared (IR), ultraviolet (UV), and nuclear magnetic resonance (NMR) spectroscopy. The structure of the complexes was confirmed by elemental analysis, IR and UV spectroscopy, and thermogravimetric analysis.

Results

Results. The Schiff base ligands containing a hydrazone moiety of (Z)-2-((E)-1-hydroxyethylidene)hydrazineylidene)-2-phenylacetic acid, as well as their praseodymium, samarium, europium, and gadolinium complexes, were synthesized using the authors’ procedure.

Conclusions

Conclusions. NMR and IR spectroscopic data confirm that the Schiff base ligand is in the keto form. There are three absorption bands in the wavelength range of 205–306 nm in the UV spectrum of the ligand. A bathochromic shift is observed in the spectrum of all complexes. The molar ratio of ligand and metal in the complexes was 3 : 1.

Цели

Цели. Синтезировать лиганды основания Шиффа, содержащие гидразоновую часть (Z)-2-((E)-1-гидроксиэтилиден)гидразинилиден)-2-фенилуксусной кислоты, и их комплексы празеодима, самария, европия и гадолиния, а также исследовать их структуру.

Методы

Методы. Структура лигандов была идентифицирована с помощью инфракрасной (ИК) и ультрафиолетовой (УФ) спектроскопии и спектроскопии ядерного магнитного резонанса (ЯМР). Структура комплексов была подтверждена с помощью элементного анализа, ИК- и УФ-спектроскопии и термогравиметрического анализа.

Результаты

Результаты. Лиганды основания Шиффа, содержащие гидразоновую часть (Z)-2-((E)-1-гидроксиэтилиден)гидразинилиден)-2-фенилуксусной кислоты, и их комплексы с празеодимом, самарием, европием и гадолинием были синтезированы по методике авторов.

Выводы

Выводы. Данные ЯМР- и ИК-спектроскопии подтверждают, что лиганд на основе Шиффа находится в кето-форме. В УФ-спектре лиганда имеются три полосы поглощения в диапазоне длин волн 205–306 нм. В спектре всех комплексов наблюдается батохромный сдвиг. Молярное соотношение лиганда и металла в комплексах составило 3 : 1.

гидразоныфенилглиоксиловая кислотаоснование Шиффаредкоземельные элементыкомплексообразованиеhydrazonesphenylglyoxylic acidSchiff baserare earth elementscomplexingReferencesGolcu A., Tumer M., Demirelli H., Wheatley R.A. Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorg. Chim. Acta. 2005;358(6):1785–1797. https://doi.org/10.1016/j.ica.2004.11.026Golcu A., Tumer M., Demirelli H., Wheatley R.A. Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorg. Chim. Acta. 2005;358(6):1785–1797. https://doi.org/10.1016/j.ica.2004.11.026Sinha D., Tiwari A.K., Singh S., Shukla G., Mishra P., Chandra H., Mishra A.K. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. Eur. J. Med. Chem. 2008;43(1): 160–165. https://doi.org/10.1016/j.ejmech.2007.03.022Sinha D., Tiwari A.K., Singh S., Shukla G., Mishra P., Chandra H., Mishra A.K. Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde. Eur. J. Med. Chem. 2008;43(1): 160–165. https://doi.org/10.1016/j.ejmech.2007.03.022Abbasova G.D., Pashajanov A.M., Ganbarova M.I., Gasanova S.M., Mammadova Z.A., Nasibova A.M. Synthesis and characterization of new metal complexes with tridentate hydrazone ligand. Azerbaijan Chemical Journal. 2023;4: 84–90. https://doi.org/10.32737/0005-2531-2023-4-84-90Abbasova G.D., Pashajanov A.M., Ganbarova M.I., Gasanova S.M., Mammadova Z.A., Nasibova A.M. Synthesis and characterization of new metal complexes with tridentate hydrazone ligand. Azerbaijan Chemical Journal. 2023;4: 84–90. https://doi.org/10.32737/0005-2531-2023-4-84-90Mohamed G.G. Synthesis, characterization and biological activity of bis(phenylimine) Schiff base ligands and their metal complexes. Spectrochim. Acta A. 2006;64(1):188–195. https://doi.org/10.1016/j.saa.2005.05.044Mohamed G.G. Synthesis, characterization and biological activity of bis(phenylimine) Schiff base ligands and their metal complexes. Spectrochim. Acta A. 2006;64(1):188–195. https://doi.org/10.1016/j.saa.2005.05.044Tofazzal M., Tarafder H., Ali M.A., Saravanan N., Weng W.Y., Kumar S., Tsafe N.U., Crouse K.A. Coordination chemistry and biological activity of two tridentate ONS and NNS Schiff bases derived from S-benzyldithiocarbazate. Trans. Met. Chem. 2000;25:295–298. https://doi.org/10.1023/A:1007044910814Tofazzal M., Tarafder H., Ali M.A., Saravanan N., Weng W.Y., Kumar S., Tsafe N.U., Crouse K.A. Coordination chemistry and biological activity of two tridentate ONS and NNS Schiff bases derived from S-benzyldithiocarbazate. Trans. Met. Chem. 2000;25:295–298. https://doi.org/10.1023/A:1007044910814Chandra S., Jain D., Sharma A.K., Sharma P. Coordination Modes of a Schiff Base Pentadentate Derivative of 4-Aminoantipyrine with Cobalt(II), Nickel(II) and Copper(II) Metal Ions: Synthesis, Spectroscopic and Antimicrobial Studies. Molecules. 2009;14(1):174–190. https://doi.org/10.3390/molecules14010174Chandra S., Jain D., Sharma A.K., Sharma P. Coordination Modes of a Schiff Base Pentadentate Derivative of 4-Aminoantipyrine with Cobalt(II), Nickel(II) and Copper(II) Metal Ions: Synthesis, Spectroscopic and Antimicrobial Studies. Molecules. 2009;14(1):174–190. https://doi.org/10.3390/molecules14010174Karmakar M., Chattopadhyay S. A comprehensive overview of the orientation of tetradentate N2O2 donor Schiff base ligands in octahedral complexes of trivalent 3d metals. J. Molec. Struct. 2019;1186:155–186. https://doi.org/10.1016/j.molstruc.2019.02.091Karmakar M., Chattopadhyay S. A comprehensive overview of the orientation of tetradentate N2O2 donor Schiff base ligands in octahedral complexes of trivalent 3d metals. J. Molec. Struct. 2019;1186:155–186. https://doi.org/10.1016/j.molstruc.2019.02.091Abu-Dief A.M., Mohamed I.M.A. A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef Univ. J. Basic Appl. Sci. 2015;4(2):119–133. https://doi.org/10.1016/j.bjbas.2015.05.004Abu-Dief A.M., Mohamed I.M.A. A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef Univ. J. Basic Appl. Sci. 2015;4(2):119–133. https://doi.org/10.1016/j.bjbas.2015.05.004More M.S., Joshi P.G., Mishra Y.K., Khanna P.K. Metal complexes driven from Schiff bases and semicarbazones for biomedical and allied applications: a review. Mater. Today. Chem. 2019;14:100195. https://doi.org/10.1016/j.mtchem.2019.100195More M.S., Joshi P.G., Mishra Y.K., Khanna P.K. Metal complexes driven from Schiff bases and semicarbazones for biomedical and allied applications: a review. Mater. Today. Chem. 2019;14:100195. https://doi.org/10.1016/j.mtchem.2019.100195Khalil M.M.H., Ismail E.H., Mohamed G.G., Zayed E.M., Badr A. Synthesis and characterization of a novel Schiff base metal complexes and their application in determination of iron in different types of natural water. Open J. Inorg. Chem. 2012;2(2):13–21. http://dx.doi.org/10.4236/ojic.2012.22003Khalil M.M.H., Ismail E.H., Mohamed G.G., Zayed E.M., Badr A. Synthesis and characterization of a novel Schiff base metal complexes and their application in determination of iron in different types of natural water. Open J. Inorg. Chem. 2012;2(2):13–21. http://dx.doi.org/10.4236/ojic.2012.22003Kajal A., Bala S., Kamboj S., Sharma N., Saini V. Schiff Bases: A Versatile Pharmacophore. J. Catalysts. 2013;2013:893512. https://doi.org/10.1155/2013/893512Kajal A., Bala S., Kamboj S., Sharma N., Saini V. Schiff Bases: A Versatile Pharmacophore. J. Catalysts. 2013;2013:893512. https://doi.org/10.1155/2013/893512Alsaygh A., Al-Humaidi J., Al-Najjar I. Synthesis of Some New Pyridine-2-yl-Benzylidene-Imines. Int. J. Org. Chem. 2014;4(2). http://doi.org/10.4236/ijoc.2014.42013Alsaygh A., Al-Humaidi J., Al-Najjar I. Synthesis of Some New Pyridine-2-yl-Benzylidene-Imines. Int. J. Org. Chem. 2014;4(2). http://doi.org/10.4236/ijoc.2014.42013Utreja D., Vibha B.S.P., Singh S., Kaur M. Schiff Bases and their Metal Complexes as Anti-Cancer Agents: A Review. Current Bioactive Compounds. 2015;11(4):215–230. http://doi.org/10.2174/1573407212666151214221219Utreja D., Vibha B.S.P., Singh S., Kaur M. Schiff Bases and their Metal Complexes as Anti-Cancer Agents: A Review. Current Bioactive Compounds. 2015;11(4):215–230. http://doi.org/10.2174/1573407212666151214221219Chaudhary N.K. Synthesis and medicinal use of Metal complexes of Schiff Bases. Bibechana. 2013;9:75–80. https://doi.org/10.3126/bibechana.v9i0.7178Chaudhary N.K. Synthesis and medicinal use of Metal complexes of Schiff Bases. Bibechana. 2013;9:75–80. https://doi.org/10.3126/bibechana.v9i0.7178Sheikhshoaie I., Ebrahimipour S.Y., Sheikhshoaie M., Rudbari H.A., Khaleghi M., Bruno G. Combined experimental and theoretical studies on the X-ray crystal structure, FT-IR, 1HNMR, 13CNMR, UV–Vis spectra, NLO behavior andantimicrobial activity of 2-hydroxyacetophenone benzoylhydrazone. Spectrochim. Acta A. 2014;124:548–555. https://doi.org/10.1016/j.saa.2014.01.043Sheikhshoaie I., Ebrahimipour S.Y., Sheikhshoaie M., Rudbari H.A., Khaleghi M., Bruno G. Combined experimental and theoretical studies on the X-ray crystal structure, FT-IR, 1HNMR, 13CNMR, UV–Vis spectra, NLO behavior andantimicrobial activity of 2-hydroxyacetophenone benzoylhydrazone. Spectrochim. Acta A. 2014;124:548–555. https://doi.org/10.1016/j.saa.2014.01.043Krishnamoorthy P., Sathyadevi P., Butorac R.R.,.Cowley A.H, Bhuvanesh N.S., Dharmaraj N. Copper(I) and nickel(II) complexes with 1 : 1 vs. 1 : 2 coordination of ferrocenyl hydrazone ligands: Do the geometry and composition of complexes affect DNA binding/cleavage, protein binding, antioxidant and cytotoxic activities? Dalton Trans. 2012;41:4423–4436. https://doi.org/10.1039/C2DT11938BKrishnamoorthy P., Sathyadevi P., Butorac R.R.,.Cowley A.H, Bhuvanesh N.S., Dharmaraj N. Copper(I) and nickel(II) complexes with 1 : 1 vs. 1 : 2 coordination of ferrocenyl hydrazone ligands: Do the geometry and composition of complexes affect DNA binding/cleavage, protein binding, antioxidant and cytotoxic activities? Dalton Trans. 2012;41:4423–4436. https://doi.org/10.1039/C2DT11938BSharma M., Chauhan K., Srivastava R.K., Singh S.V., Srivastava K., Saxena J.K., Puri S.K., Chauhan P. Design and Synthesis of a New Class of 4-Aminoquinolinyl- and 9-Anilinoacridinyl Schiff Base Hydrazones as Potent Antimalarial Agents. Chem. Biol. Drug Des. 2014;84(2): 175–181. https://doi.org/10.1111/cbdd.12289Sharma M., Chauhan K., Srivastava R.K., Singh S.V., Srivastava K., Saxena J.K., Puri S.K., Chauhan P. Design and Synthesis of a New Class of 4-Aminoquinolinyl- and 9-Anilinoacridinyl Schiff Base Hydrazones as Potent Antimalarial Agents. Chem. Biol. Drug Des. 2014;84(2): 175–181. https://doi.org/10.1111/cbdd.12289Vyas K.M., Jadeja R., Patel D., Devkar R., Gupta V.K. A new pyrazolone based ternary Cu(II) complex: Synthesis, characterization, crystal structure, DNA binding, protein binding and anti-cancer activity towards A549 human lung carcinoma cells with a minimum cytotoxicity to non-cancerous cells. Polyhedron. 2013;65:262–274. https://doi.org/10.1016/j.poly.2013.08.051Vyas K.M., Jadeja R., Patel D., Devkar R., Gupta V.K. A new pyrazolone based ternary Cu(II) complex: Synthesis, characterization, crystal structure, DNA binding, protein binding and anti-cancer activity towards A549 human lung carcinoma cells with a minimum cytotoxicity to non-cancerous cells. Polyhedron. 2013;65:262–274. https://doi.org/10.1016/j.poly.2013.08.051Kratz F., Beyer U., Roth T., Tarasova N., Collery P., Lechenault F., Cazabat A., Schumcher P., Unger C., Falken U. Transferrin Conjugates of Doxorubicin: Synthesis, Characterization, Cellular Uptake, and in Vitro Efficacy. J. Pharm. Sci. 1998;87(3): 338–346. https://doi.org/10.1021/js970246aKratz F., Beyer U., Roth T., Tarasova N., Collery P., Lechenault F., Cazabat A., Schumcher P., Unger C., Falken U. Transferrin Conjugates of Doxorubicin: Synthesis, Characterization, Cellular Uptake, and in Vitro Efficacy. J. Pharm. Sci. 1998;87(3): 338–346. https://doi.org/10.1021/js970246aJaividhya P., Dhivya R., Akbarsha M.A., Palaniandavar M. Efficient DNA cleavage mediated by mononuclear mixed ligand copper(II) phenolate complexes: The role of co-ligand planarity on DNA binding and cleavage and anticancer activity. J. Inorg. Biochem. 2012;114:94–105. https://doi.org/10.1016/j.jinorgbio.2012.04.018Jaividhya P., Dhivya R., Akbarsha M.A., Palaniandavar M. Efficient DNA cleavage mediated by mononuclear mixed ligand copper(II) phenolate complexes: The role of co-ligand planarity on DNA binding and cleavage and anticancer activity. J. Inorg. Biochem. 2012;114:94–105. https://doi.org/10.1016/j.jinorgbio.2012.04.018Apelgot S., Coppey J., Fromentin A., Guille E., Poupon M., Roussel A. Altered distribution of copper (64Cu) in tumorbearing mice and rats. Anticancer Res. 1986;6(2):159–164. https://europepmc.org/article/med/3707051#impactApelgot S., Coppey J., Fromentin A., Guille E., Poupon M., Roussel A. Altered distribution of copper (64Cu) in tumorbearing mice and rats. Anticancer Res. 1986;6(2):159–164. https://europepmc.org/article/med/3707051#impactHasinoff B.B., Yadav A.A., Patel D., Wu X. The cytotoxicity of the anticancer drug elesclomol is due to oxidative stress indirectly mediated through its complex with Cu(II). J. Inorg. Biochem. 2014;137:22–30. https://doi.org/10.1016/j.jinorgbio.2014.04.004Hasinoff B.B., Yadav A.A., Patel D., Wu X. The cytotoxicity of the anticancer drug elesclomol is due to oxidative stress indirectly mediated through its complex with Cu(II). J. Inorg. Biochem. 2014;137:22–30. https://doi.org/10.1016/j.jinorgbio.2014.04.004Ebrahimipour S.Y., Sheikhshoaie I., Crochet A., Khaleghi M., Fromm K.M. A new mixed-ligand copper(II) complex of (E)-N′-(2-hydroxybenzylidene) acetohydrazide: Synthesis, characterization, NLO behavior, DFT calculation and biological activities. J. Mol. Struct. 2014;1072:267–276. https://doi.org/10.1016/j.molstruc.2014.05.024Ebrahimipour S.Y., Sheikhshoaie I., Crochet A., Khaleghi M., Fromm K.M. A new mixed-ligand copper(II) complex of (E)-N′-(2-hydroxybenzylidene) acetohydrazide: Synthesis, characterization, NLO behavior, DFT calculation and biological activities. J. Mol. Struct. 2014;1072:267–276. https://doi.org/10.1016/j.molstruc.2014.05.024Marzano C., Pellei M., Tisato F., Santini C. Copper complexes as anticancer agents. Anticancer Agents Med. Chem. 2009;9(2): 185–211. https://doi.org/10.2174/187152009787313837Marzano C., Pellei M., Tisato F., Santini C. Copper complexes as anticancer agents. Anticancer Agents Med. Chem. 2009;9(2): 185–211. https://doi.org/10.2174/187152009787313837Garbutcheon-Singh K.B., Grant M.P., Harper B.W., Krause-Heuer A.M., Manohar M., Orkey N., AldrichWright J.R. Transition Metal Based Anticancer Drugs. Curr. Top. Med. Chem. 2011;11(5):521–542. https://doi.org/10.2174/156802611794785226Garbutcheon-Singh K.B., Grant M.P., Harper B.W., Krause-Heuer A.M., Manohar M., Orkey N., AldrichWright J.R. Transition Metal Based Anticancer Drugs. Curr. Top. Med. Chem. 2011;11(5):521–542. https://doi.org/10.2174/156802611794785226Vogel H.G. (Ed.). Drug Discovery and Evaluation: Pharmacological Assays. Berlin: Springer; 2008. 2068 p. http://dx.doi.org/10.1007/978-3-540-70995-4Vogel H.G. (Ed.). Drug Discovery and Evaluation: Pharmacological Assays. Berlin: Springer; 2008. 2068 p. http://dx.doi.org/10.1007/978-3-540-70995-4Ebrahimipour S.Y., Sheikhshoaie I., Castro J., Haase W., Mohamadi M., Foro S., Sheikhshoaie M., Mahani S.E. A novel cationic copper(II) Schiff base complex: Synthesis, characterization, crystal structure, electrochemical evaluation, anti-cancer activity, and preparation of its metal oxide nanoparticles. Inorganica Chimica Acta. 2015;430:245–252. https://doi.org/10.1016/j.ica.2015.03.016Ebrahimipour S.Y., Sheikhshoaie I., Castro J., Haase W., Mohamadi M., Foro S., Sheikhshoaie M., Mahani S.E. A novel cationic copper(II) Schiff base complex: Synthesis, characterization, crystal structure, electrochemical evaluation, anti-cancer activity, and preparation of its metal oxide nanoparticles. Inorganica Chimica Acta. 2015;430:245–252. https://doi.org/10.1016/j.ica.2015.03.016Sheikhshoaie I., Ebrahimipour S.Y., Sheikhshoaie M., Mohamadi M., Abbasnejad M., Rudbari H.A., Bruno G. Synthesis, characterization, X-ray crystal structure, electrochemical evaluation and anti-cancer studies of a mixed ligand Cu(II) complex of (E)-N′-((2-hydroxynaphthalen-1yl)methylene)acetohydrazide J. Chem. Sci. 2015;127(12): 2193–2200. https://doi.org/10.1007/s12039-015-0978-8Sheikhshoaie I., Ebrahimipour S.Y., Sheikhshoaie M., Mohamadi M., Abbasnejad M., Rudbari H.A., Bruno G. Synthesis, characterization, X-ray crystal structure, electrochemical evaluation and anti-cancer studies of a mixed ligand Cu(II) complex of (E)-N′-((2-hydroxynaphthalen-1yl)methylene)acetohydrazide J. Chem. Sci. 2015;127(12): 2193–2200. https://doi.org/10.1007/s12039-015-0978-8Guliyeva E.A., Fatullayeva P.A., Hagverdiyeva T.M. Synthesis and studies of Cu(II), Ni(II), Co(II) complexes with bis(saliciliden)hydrazon. Azerbaijan Chemical Journal. 2023;2:116–122. https://doi.org/10.32737/0005-2531-2023-2-116-122Guliyeva E.A., Fatullayeva P.A., Hagverdiyeva T.M. Synthesis and studies of Cu(II), Ni(II), Co(II) complexes with bis(saliciliden)hydrazon. Azerbaijan Chemical Journal. 2023;2:116–122. https://doi.org/10.32737/0005-2531-2023-2-116-122Abbasova G., Medjidov A. One-pot Synthesis of a New Hydroxamic Acid and its Complexes with Metals. Letters in Organic Chemistry. 2022;19(10):837–841. http://doi.org/10.2174/1570178619666220111121743Abbasova G., Medjidov A. One-pot Synthesis of a New Hydroxamic Acid and its Complexes with Metals. Letters in Organic Chemistry. 2022;19(10):837–841. http://doi.org/10.2174/1570178619666220111121743Sarwar A., Shamsuddin M.B., Lingtang H. Synthesis, Characterization and Luminescence Studies of Metal-Diimine Complexes. Mod. Chem. Appl. 2018;6(3):1000262. http://doi.org/10.4172/2329-6798.1000262Sarwar A., Shamsuddin M.B., Lingtang H. Synthesis, Characterization and Luminescence Studies of Metal-Diimine Complexes. Mod. Chem. Appl. 2018;6(3):1000262. http://doi.org/10.4172/2329-6798.1000262Naemi H., Moradian M. Synthesis and characterization of nitro-Schiff bases derived from 5-nitro-salicylaldehyde and various diamines and their complexes of Co(II). J. Coord. Chem. 2010;63(1):156–162. http://doi.org/10.1080/00958970903225866Naemi H., Moradian M. Synthesis and characterization of nitro-Schiff bases derived from 5-nitro-salicylaldehyde and various diamines and their complexes of Co(II). J. Coord. Chem. 2010;63(1):156–162. http://doi.org/10.1080/00958970903225866Nakamoto K. Infrared and Raman spectra of Inorganic and Coordination Compounds. Wiley; 1991. 410 p.Nakamoto K. Infrared and Raman spectra of Inorganic and Coordination Compounds. Wiley; 1991. 410 p.Calinescu M., Manea L., Pavelescu G. Synthesys and spectroscopic properties of new complex compounds of europium(III) and terbium(III) with 2-hydroxy-1naphthaldehyde acetylhydrazone and heterocyclic bases. Rev. Roum.Chim. 2011;56(3):231–237. http://web.icf.ro/rrch/Calinescu M., Manea L., Pavelescu G. Synthesys and spectroscopic properties of new complex compounds of europium(III) and terbium(III) with 2-hydroxy-1naphthaldehyde acetylhydrazone and heterocyclic bases. Rev. Roum.Chim. 2011;56(3):231–237. http://web.icf.ro/rrch/Tarasevich B.N. IK spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of the Main Classes of Organic Compounds). Moscow; MSU; 2012. 54 p. (in Russ.).Tarasevich B.N. IK spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of the Main Classes of Organic Compounds). Moscow; MSU; 2012. 54 p. (in Russ.).

The authors declare that there are no conflicts of interest present.