Abstract
A new azomethine compound 4-methyl-N-[2-pentafluorophenyliminomethyl)phenyl]methylbenzenesulfamide and a Cu(II) complex based on it are obtained and characterized by 1H NMR, IR spectroscopy and the elemental analysis. Crystal structures of azomethine and its complex are analyzed by single crystal X-ray diffraction (XRD). From the single crystal XRD data it is found that the Cu(II) complex crystallizes in the triclinic space group \(P\bar{1}\). The unit cell contains two crystallographically independent mononuclear molecules with similar geometries. In the complex, copper ions have a distorted tetrahedral environment of four nitrogen atoms, which is formed by two bidentate coordinated azomethine ligands. From magnetic measurements it is found that the Cu(II) complex is paramagnetic.
REFERENCES
A. M. Abu-Dief and I. M. A. Mohamed. A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef Univ. J. Basic Appl. Sci., 2015, 4, 119. https://doi.org/10.1016/j.bjbas.2015.05.004
A. Soroceanu and A. Bargan. Advanced and biomedical applications of Schiff-base ligands and their metal complexes: A review. Crystals, 2022, 12, 1436. https://doi.org/10.3390/cryst12101436
Schiff Base in Organic, Inorganic and Physical Chemistry / Ed. T. Akitsu. IntechOpen, 2023. https://doi.org/10.5772/intechopen.104134
W. Zoubi. Biological activities of schiff bases and their complexes: A review of recent works. Inter. J. Org. Chem., 2013, 3, 73. https://doi.org/10.4236/ijoc.2013.33A008
I. Tsacheva, Z. Todorova, D. Momekova, G. Momekov, and N. Koseva. Pharmacological activities of Schiff bases and their derivatives with low and high molecular phosphonates. Pharmaceuticals, 2023, 16, 938. https://doi.org/10.3390/ph16070938
J. Ceramella, D. Iacopetta, A. Catalano, F. Cirillo, R. Lappano, and M. S. Sinicropi. A review on the antimicrobial activity of Schiff bases: Data collection and recent studies. Antibiotics, 2022, 11(2), 191. https://doi.org/10.3390/antibiotics11020191
M. Pervaiz, A. Munir, A. Riaz, Z. Saeed, U. Younas, M. Imran, S. Ullah, R. Bashir, A. Rashid, and A. Adnan. Review article: Amalgamation, scrutinizing, and biological evaluation of the antimicrobial aptitude of thiosemicarbazide Schiff bases derivatives metal complexes. Inorg. Chem. Commun., 2022, 141, 109459. https://doi.org/10.1016/j.inoche.2022.109459
R. Kumar, A. Abha Singh, U. Kumar, P. Jain, A. Kumar Sharma, C. Kant, and M. S. Haque Faizi. Recent advances in synthesis of heterocyclic Schiff base transition metal complexes and their antimicrobial activities especially antibacterial and antifungal. J. Mol. Struct., 2023, 1294, 136346. https://doi.org/10.1016/j.molstruc.2023.136346
B. G. Tweedy. Plant extracts with metal ions as potential antimicrobial agents. Phytopatology, 1964, 55, 910.
S. Q. Memon, N. Memon, A. Mallah, R. Soomro, and M. Y. Khuhawar. Schiff bases as chelating reagents for metal ions analysis. Curr. Anal. Chem., 2014, 10, 393. https://doi.org/10.2174/157341101003140521113731
A. L. Berhanu, Gaurav, I. Mohiuddin, A. Kumar Malik, J. Singh Aulakh, V. Kumar, and Ki-Hyun Kim. A review of the applications of Schiff bases as optical chemical sensors. Trends Anal. Chem., 2019, 116, 74. https://doi.org/10.1016/j.trac.2019.04.025
V. K. Juyal, A. Pathak, M. Panwar, S. C. Thakuri, O. Prakash, A. Agrwal, and V. Nand. Schiff base metal complexes as a versatile catalyst: A review. J. Organomet. Chem., 2023, 999, 122825. https://doi.org/10.1016/j.jorganchem.2023.122825
K. C. Gupta and A. K. Sutar. Catalytic activities of Schiff base transition metal complexes. Coord. Chem. Rev., 2008, 252, 1420-1450 https://doi.org/10.1016/j.ccr.2007.09.005
A. S. Burlov, Yu. V. Koshchienko, V. N. Ikorskii, V. G. Vlasenko, I. A. Zarubin, A. I. Uraev, I. S. Vasil′chenko, D. A. Ganovskii, G. S. Borodkin, S. A. Nikolaevskii, and A. D. Garnovskii. New magnetoactive copper complexes with Schiff′s bases. Russ. J. Inorg. Chem., 2006, 51, 1065. https://doi.org/10.1134/S0036023606070096
A. S. Burlov, S. A. Nikolaevskii, A. S. Bogomyakov, I. S. Vasil′chenko, Y. V. Koshchienko, V. G. Vlasenko, A. I. Uraev, D. A. Garnovskii, E. V. Sennikova, G. S. Borodkin, A. D. Garnovskii, and V. I. Minkin. New magnetically active metal complexes of tridentate Schiff bases of phenylazosalicylaldehyde. Russ. J. Coord. Chem., 2009, 35, 486. https://doi.org/10.1134/S1070328409070045
Yu. P. Tupolova, V. A. Kogan, V. V. Lukov, L. D. Popov, I. E. Gevorkyan, and V. G. Vlasenko. Synthesis and magnetic properties of the novel binuclear copper(II) metallochelates with unsymmetrical exchange fragment including heterocyclic derivatives. Transition Met. Chem., 2007, 32, 656. https://doi.org/10.1007/s11243-007-0218-2
A. S. Burlov, V. G. Vlasenko, D. A. Garnovskii, N. V. Polosareva, A. S. Antsyshkina, G. G. Sadikov, V. S. Sergienko, A. V. Churakov, Ya. V. Zubavichus, E. I. Mal′tsev, A. V. Dmitriev, D. A. Lypenko, A. S. Cheprasov, G. S. Borodkin, and A. V. Metelitsa. Synthesis, crystal structure, and electroluminescent properties of zinc and cadmium tetradentate azomethine complexes. Russ. J. Inorg. Chem., 2014, 59, 721. https://doi.org/10.1134/S0036023614070031
A. S. Burlov, V. G. Vlasenko, Yu. V. Koshchienko, N. I. Makarova, A. A. Zubenko, Yu. D. Drobin, G. S. Borodkin, A. V. Metelitsa, Ya. V. Zubavichus, and D. A. Garnovskii. Complexes of zinc(II) with N-[2-(hydroxylalkyliminomethyl)phenyl]-4-methylbenzenesulfonamides: Synthesis, structure, photoluminescence properties and biological activity. Polyhedron, 2018, 144, 249. https://doi.org/10.1016/j.poly.2018.01.020
A. S. Burlov, E. I. Mal′tsev, V. G. Vlasenko, D. A. Garnovskii, A. V. Dmitriev, D. A. Lypenko, A. V. Vannikov, P. V. Dorovatovskii, V. A. Lazarensko, Ya. V. Zubavichus, and V. N. Khrustalev. Synthesis, structure, photo- and electroluminescent properties of bis{(4-methyl-N-[2-[(E)-2-pyridyliminmethyl]phenyl)]benzenesulfonamide}zinc(II). Polyhedron, 2017, 133, 231. https://doi.org/10.1016/j.poly.2017.05.045
A. S. Burlov, V. G. Vlasenko, M. S. Milutka, Y. V. Koshchienko, N. I. Makarova, V. A. Lazarenko, A. L. Trigub, A. A. Kolodina, A. A. Zubenko, A. V. Metelitsa, D. A. Garnovskii, A. N. Gusev, and W. Linert. Synthesis, structure, spectral-luminescent properties, and biological activity of chlorine-substituted N-[2-(phenyliminomethyl)phenyl]-4-methylbenzenesulfamide and their zinc(II) complexes. Inter. J. Mol. Sci., 2022, 23, 15259. https://doi.org/10.3390/ijms232315259.
E. Yao, J. Wang, Z. Chen, and Y. Ma. Homo- and heteroligated salicylaldiminato titanium complexes with different substituents ortho to the phenoxy oxygens for ethylene and ethylene/1-hexene (co)polymerization. Macromolecules, 2014, 47, 8164. https://doi.org/10.1021/ma5017677
K. V. Axenov, M. Klinga, O. Lehtonen, H. T. Koskela, M. Leskela, and T. Repo. Hafnium bis(phenoxyimino) dibenzyl complexes and their activation toward olefin polymerization. Organometallics, 2007, 26, 1444. https://doi.org/10.1021/om060753f
L. Annunziata, D. Pappalardo, C. Tedesco, and C. Pellecchia. Octahedral bis(phenoxy-imine)tin(IV) alkyl complexes: Synthesis, characterization, and reactivity toward ionizing species and ethylene. Organometallics, 2005, 24, 1947. https://doi.org/10.1021/om0491084
D. R. Meena, Deepa, M. J. Aalam, P. Chaudhary, G. D. Yadav, and S. Singh. Synthesis and structural studies of Pd(II) complexes of bidentate Schiff bases and their catalytic activities as pre-catalysts in the Mizoroki-Heck reaction. Polyhedron, 2022, 222, 115931. https://doi.org/10.1016/j.poly.2022.115931
S. Lin, H. Pan, L. Li, R. Liao, S. Yu, Q. Zhao, H. Sun, and W. Huang. AIPE-active platinum(II) complexes with tunable photophysical properties and their application in constructing thermosensitive probes used for intracellular temperature imaging. J. Mater. Chem. C, 2019, 7, 7893. https://doi.org/10.1039/c9tc01905g
V. G. Vlasenko, A. S. Burlov, Y. V. Koshchienko, M. A. Kiskin, D. A. Garnovskii, Y. V. Zubavichus, A. A. Kolodina, A. L. Trigub, A. A. Zubenko, and Y. D. Drobin. Synthesis, characterization, and biological activity of Co(II), Ni(II), and Cu(II) complexes derived from N,N′-bis(2-N-tozylaminobenzylidene)diaminodipropyliminate ligand. Inorg. Chim. Acta, 2020, 510, 119776. https://doi.org/10.1016/j.ica.2020.119766
V. G. Vlasenko, A. S. Burlov, Y. V. Koshchienko, A. A. Kolodina, S. P. Kubrin, B. V. Chaltsev, Y. V. Zubavichus, V. A. Lazarenko, A. A. Zubenko, and A. I. Klimenko. Synthesis, structural characterization, and biological activities of mononuclear Fe(II), Mn(II), and Ni(II) complexes derived from N-[2-(2-diethylaminoethyliminomethyl)phenyl]-4-methylbenzenesulfonamide. J. Mol. Struct., 2022, 1247, 131370. https://doi.org/10.1016/j.molstruc.2021.131370
V. G. Vlasenko, A. S. Burlov, Y. V. Koshchienko, A. A. Kolodina, Y. V. Zubavichus, V. N. Khrustalev, T. N. Danilenko, A. A. Zubenko, L. N. Fetisov, and A. I. Klimenko. Synthesis, X-ray structure and biological activity of mono- and dinuclear copper complexes derived from N-{2-[(2-diethylamino(ethyl or propyl)imino)-methyl]-phenyl}-4-methyl-benzenesulfonamide. Inorg. Chim. Acta, 2021, 523, 120408. https://doi.org/10.1016/j.ica.2021.120408
N. I. Chernova, Yu. S. Ryabokobylko, V. G. Brudz′, and B. M. Bolotin. 2-(N-tozilamino)benzal′degid i ego zamestitel′noe proizvodnoe (2-(N-tosylamino)benzaldehyde and substitute derivative). Zh. Org. Khim., 1971, 7, 1680. [In Russian]
N. E. Gelman, E. A. Terentyeva, T. M. Shanina, and L. M. Kiparenko. Metody kolichestvennogo organicheskogo elementnogo analiza (Methods of Quantitative Organic Elemental Analysis). Moscow, Russia: Khimiya, 1987. [In Russian]
APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A). Madison, Wisconsin, USA: Bruker Advansed X-Ray Solutions, 2006.
G. M. Sheldrick. Crystal structure refinement with SHELXL. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71(1), 3-8. https://doi.org/10.1107/s2053229614024218
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr., 2009, 42, 339. https://doi.org/10.1107/S0021889808042726
G. M. Sheldrick. SADABS-2004/1: Program for Scaling and Correction of Area Detector Data. Göttinngen, Germany: Göttingen University, 2004.
A. L. Spek. PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr., Sect. A: Found. Crystallogr., 1990, 46, c34.
Yu. P. Dormidontov. Metody UF, IK i YaMR spektroskopii i ikh primenenie v organicheskoi khimii (Methods of UV, IR and NMR Spectroscopy and Their Application in Organic Chemistry). Perm, Russia: Perm. Univ., 2008.
K. Nakanishi. Infrared Absorption Spectroscopy. San Francisco, USA: Holden-Day, 1962.
D. A. Garnovskii, M. F. C. Guedes da Silva, M. N. Kopylovich, A. D. Garnovskii, J. J. R. Frausto da Silva, and A. J. L. Pombeiro. Electrochemical synthesis of adducts of 2-aminopyridine or methanol in metal chelates of a N,N,N-tridentate Schiff base ligand. X-ray crystal structures of the Ni(II) and Zn(II) derivatives. Polyhedron, 2003, 22, 1335. https://doi.org/10.1016/S0277-5387(03)00104-9
E. Labisbal, L. Rodríguez, A. Sousa-Pedrares, M. Alonso, A. Vizoso, J. Romero, J. A. García-Vázquez, and A. Sousa. Synthesis, characterisation and X-ray structures of diorganotin(IV) and iron(III) complexes of dianionic terdentate Schiff base ligands. J. Organomet. Chem., 2006, 691, 1321. https://doi.org/10.1016/j.jorganchem.2005.09.052
V. G. Vlasenko, A. S. Burlov, M. A. Kiskin, S. A. Nikolaevsky, Yu. V. Koshchienko, and A. A. Shiryaeva. Synthesis and structure of Cu(II) and Co(II) complexes with N-{2-[(E)-(4-cyclohexylphenyl)iminomethyl]phenyl}-4-methylbenzene-1-sulfonamide. J. Struct. Chem., 2023, 64(5), 906. https://doi.org/10.1134/S0022476623050098
L. Yang, D. R. Powell, and R. P. Houser. Structural variation in copper(I) complexes with pyridylmethylamide ligands: Structural analysis with a new four-coordinate geometry index, τ4. Dalton Trans., 2007, 9, 955. https://doi.org/10.1039/b617136b
J. Cirera, P. Alemany, and S. Alvarez. Mapping the stereochemistry and symmetry of tetracoordinate transition-metal complexes. Chem. Eur. J., 2004, 10, 190. https://doi.org/10.1002/chem.200305074
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The work was supported by the Ministry of Science and Higher Education of the Russian Federation (state assignment in the research field No. FENW-2023-0014, 2023).
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Russian Text © The Author(s), 2024, published in Zhurnal Strukturnoi Khimii, 2024, Vol. 65, No. 2, 121603.https://doi.org/10.26902/JSC_id121603
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Vlasenko, V.G., Burlov, A.S., Nikolaevskii, S.A. et al. Synthesis, Structure, and Properties of 4-Methyl-N-[2-(Pentafluorophenyliminomethyl)Phenyl]Methyl-Benzenesulfamide and the Copper(II) Complex Based on It. J Struct Chem 65, 256–266 (2024). https://doi.org/10.1134/S0022476624020045
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DOI: https://doi.org/10.1134/S0022476624020045