SYNTHESIS AND CHARACTERIZATION OF COPPER(II) COMPLEX WITH 2,6-DIACETYLPYRIDINE-BIS(PHENYLHYDRAZONE)
Abstract
The syntheses, physicochemical and structural properties of the novel Cu(II) complex with 2,6-diacetylpyridine bis(phenylhydrazone) (L), of the formula [CuL2]Br2 are presented. In the reaction of warm MeOH solutions of the ligand, 2,6-diacetylpyridine bis(phenylhydrazone) and CuBr2 in molar ratio 2:1 resulted in formation of black single crystals of the bis(ligand) complex. This is the first Cu(II) complex with this ligand that is characterized by SC-XRD. Two ligand molecules are coordinated in the usual tridentate mode, via nitrogen atoms of the pyridine ring, and two azomethine nitrogen atoms, forming distorted octahedral environments of the metal ion.
References
Ainscough, E. W., Brodie, A. M., Dobbs, A. J., Ranford, J. D. & Waters, J. M. 1998. Antitumour copper(II) salicylaldehyde benzoylhydrazone (H2sb) complexes: Physicochemical properties and the single-crystal X-ray structures of [{Cu(H2sb)(CCl3CO2)2}2] and [{Cu(Hsb)(ClO4)(C2H5OH)}2]. Inorganica Chimica Acta, 267(1), pp. 27-38. https://doi.org/10.1016/s0020-1693(97)05548-5
Alvarez, S., Alemany, P., Casanova, D., Cirera, J., Llunell, M. & Avnir, D. 2005. Shape maps and polyhedral interconversion paths in transition metal chemistry. Coordination Chemistry Reviews, 249(17-18 SPEC. ISS.), pp. 1693-1708. https://doi.org/10.1016/j.ccr.2005.03.031
Armstrong, C. M., Bernhardt, P. V., Chin, P. & Richardson, D. R. 2003. Structural variations and formation constants of first-row transition metal complexes of biologically active aroylhydrazones. European Journal of Inorganic Chemistry, 2003(6), pp. 1145-1156. https://doi.org/10.1002/ejic.200390146
Avaji, P. G., Vinod Kumar, C. H., Patil, S. A., Shivananda, K. N. & Nagaraju, C. 2009. Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone. European Journal of Medicinal Chemistry, 44(9), pp. 3552-3559. https://doi.org/10.1016/j.ejmech.2009.03.032
Ávila Terra, L. H. S., Guekezian, M., Gaubeur, I., Matos, J. R. & Suárez-Iha, M. E. V. 2002. Synthesis, characterization, properties and thermal study of nickel(II)/di-2-pyridyl ketone benzoylhydrazone complex. Polyhedron, 21(23), pp. 2375-2380. https://doi.org/10.1016/S0277-5387(02)01185-3
Azaz, A. D., Celen, S., Namli, H., Turhan, O., Kurtaran, R., Kazak, C. & Arslan, N. B. 2007. Synthesis, crystal structure and biological activity of the nickel(II) complex of 2,6-diacetylpyridinedihydrazone. Transition Metal Chemistry, 32(7), pp. 884-888. https://doi.org/10.1007/s11243-007-0242-2
Bakir, M., Green, O. & Mulder, W. H. 2008. Synthesis, characterization and molecular sensing behavior of [ZnCl2(η3-N,N,O-dpkbh)] (dpkbh = di-2-pyridyl ketone benzoyl hydrazone). Journal of Molecular Structure, 873(1–3), pp. 17-28. https://doi.org/10.1016/j.molstruc.2007.03.001
Basu, C., Chowdhury, S., Banerjee, R., Stoeckli Evans, H. & Mukherjee, S. 2007. A novel blue luminescent high-spin iron(III) complex with interlayer O-H⋯Cl bridging: Synthesis, structure and spectroscopic studies. Polyhedron, 26(14), pp. 3617-3624. https://doi.org/10.1016/j.poly.2007.03.053
Belošević, S., Rodić, M., Radanović, M., & Leovac, V. 2018. Synthesis and structure of cobalt(II) complex with 2,6-diacetylpyridine-bis(phenylhydrazone). The University Thought - Publication in Natural Sciences, 8(2), pp. 33-38. https://doi.org/10.5937/univtho8-19451
Bernhardt, P. V., Chin, P., Sharpe, P. C. & Richardson, D. R. 2007. Hydrazone chelators for the treatment of iron overload disorders: Iron coordination chemistry and biological activity. Dalton Transactions, 30, pp. 3232-3244. https://doi.org/10.1039/b704102k
Buss, J. L., Greene, B. T., Turner, J., Torti, F. M. & Torti, S. V. 2005. Iron chelators in cancer chemotherapy. Current Topics in Medicinal Chemistry, 4(15), pp. 1623-1635. https://doi.org/10.2174/1568026043387269
Curry, J. D., Robinson, M. A. & Busch, D. H. 1967. Metal complexes derived from substituted hydrazones of 2,6-diacetylpyridine. Inorganic Chemistry, 6(8), pp. 1570-1574. https://doi.org/10.1021/ic50054a032
Donnelly, P. S., Caragounis, A., Du, T., Laughton, K. M., Volitakis, I., Cherny, R. A., Sharples, R. A., Hill, A. F., Li, Q. X., Masters, C. L., Barnham, K. J. & White, A. R. 2008. Selective intracellular release of copper and zinc ions from bis(thiosemicarbazonato) complexes reduces levels of Alzheimer disease amyloid-β peptide. Journal of Biological Chemistry, 283(8), pp. 4568-4577. https://doi.org/10.1074/jbc.M705957200
Dumitru, F., Legrand, Y.-M., Barboiu, M., Petit, E. & Lee, A. van der. 2009. Metallosupramolecular architectures of pseudoterpyridine-type ligands and ZnII metal ions. Crystal Growth & Design, 9(6), pp. 2917-2921. https://doi.org/10.1021/cg9002466
Geary, W. J. 1971. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 7(1), pp. 81-122. https://doi.org/10.1016/S0010-8545(00)80009-0
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. 2016. The Cambridge Structural Database. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, 72(2), pp. 171-179. https://doi.org/10.1107/S2052520616003954
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. 2011. ShelXle: A Qt graphical user interface for SHELXL. Journal of Applied Crystallography, 44(6), pp. 1281-1284. https://doi.org/10.1107/S0021889811043202
Kazak, C., Arslan, N. B., Karabulut, S., Azaz, A. D., Namlı, H. & Kurtaran, R. 2009. Supramolecular lead(II) azide complex of 2,6-diacetylpyridine dihydrazone: synthesis, molecular structure, and biological activity. Journal of Coordination Chemistry, 62(18), pp. 2966-2973. https://doi.org/10.1080/00958970902980537
Kitaev, I. & Buzykin, B. 1974. Gidrazony. Moscow: Nauka.
Kogan, V. A., Zelentsov, V. V., Larin, G. M., Lukov, V. V. 1990. Kompleksy perekhodnykh metallov c gidrazomani. Moscow: Nauka.
Llunell, M., Casanova, D., Cirera, J., Alemany, P. & Alvarez, S. 2013.SHAPE (2.1), Universitat de Barcelona, Barcelona,
Mahalingam, V., Chitrapriya, N., Fronczek, F. R., & Natarajan, K. 2008. New Ru(II)-dmso complexes with heterocyclic hydrazone ligands towards cancer chemotherapy. Polyhedron, 27(7), pp. 1917-1924. https://doi.org/10.1016/j.poly.2008.02.036
Pinto, J. J., Moreno, C., & García-Vargas, M. 2004. A very sensitive flow system for the direct determination of copper in natural waters based on spectrophotometric detection. Talanta, 64(2), pp. 562-565. https://doi.org/10.1016/j.talanta.2004.03.009
Rigaku Oxford Diffraction. 2015. CrysAlisPro Software system (1.171.38.46).
Sheldrick, G. M. 2015a. Crystal structure refinement with SHELXL. Acta Crystallographica Section C Structural Chemistry, 71(1), pp. 3-8. https://doi.org/10.1107/S2053229614024218
Sheldrick, G. M. 2015b. SHELXT - Integrated space-group and crystal-structure determination. Acta Crystallographica Section A Foundations and Advances, 71(1), pp. 3-8. https://doi.org/10.1107/S2053273314026370
Sreeja, P. B., Sreekanth, A., Nayar, C. R., Prathapachandra, M. R., Usman, K. A., Razak, I. A., Chantrapromma, S. & Fun, H. K. 2003. Synthesis, spectral studies and structure of 2-hydroxyacetophenone nicotinic acid hydrazone. Journal of Molecular Structure, 645(2-3), pp. 221-226. https://doi.org/10.1016/S0022-2860(02)00563-X
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. 2017. CrystalExplorer17 (No. 17). University of Western Australia.
Wang, B. dui, Yang, Z. Y., Crewdson, P., & Wang, D. qi. 2007. Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxychromone-3-carbaldehyde benzoyl hydrazone. Journal of Inorganic Biochemistry, 101(10), pp. 1492-1504. https://doi.org/10.1016/j.jinorgbio.2007.04.007
Watanabe, K., Mino, T., Yoshida, Y. & Sakamoto, M. 2018. Hydrazone-palladium catalyzed reactions using allyl compounds. Journal of Synthetic Organic Chemistry, Japan, 76(8), pp. 828-837. https://doi.org/10.5059/yukigoseikyokaishi.76.828
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