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Synthesis and Characterization of Mn(II), Fe(III), Co(II), Ni(II) and Cu(II) Complexes of b-Diketone
Corresponding Author(s) : Anjali S. Rajbhoj
Asian Journal of Chemistry,
Vol. 29 No. 11 (2017): Vol 29 Issue 11
Abstract
It is well known that b-diketones are also formed through Baker-Venkataraman transformation. In the present case, 3-bromo-2-methylbenzoic acid reacts with ortho-hydroxyacetophenone at room temperature to yield ester. Ester on further Baker-Venkataraman transformation yields 1,3-diketone (L) i.e. 1-(3-bromo-2-methylphenyl)-3-hydroxy-3-(2-hydroxyphenyl)prop-2-en-1-one. Five complexes of Mn(II), Fe(III), Co(II), Ni(II) and Cu(II) with bidentate ligand (L), have been synthesized from reaction of the ligand (L) with respective metal nitrates. b-diketone exhibits keto-enol tautomerism, their keto-enol tautomerism was studied in solution by IR and NMR spectroscopy. Due to enolization b-diketone acts as ligand and hence used to synthesized Mn(II), Fe(III), Co(II), NI(II) and Cu(II) complexes. The synthesized ligand has been characterized by elemental analysis, 1H, 13C NMR, LC-MS and FT-IR. The magnetic susceptibility and solution conductivity were also studied. The synthesized complexes were also studied antimicrobial screening.
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References
A.C. Swallow and M.R. Truter, Proc. R. Soc. Lond. A Math. Phys. Sci., 254, 205 (1960); https://doi.org/10.1098/rspa.1960.0015.
F.P. Dwyer and D.P. Mellor, Chelating Agents and Metal Chelates, Academic Press, London, pp. 33-64 (1964).
F. Bonati, Organomet. Chem. Rev., 1, 379 (1966).
R.M. Pike, Coord. Chem. Rev., 2, 163 (1967); https://doi.org/10.1016/S0010-8545(00)80203-9.
D. Gibson, Coord. Chem. Rev., 4, 225 (1969); https://doi.org/10.1016/S0010-8545(00)80087-9.
U. Casellato, M. Vidali and P.A. Vigato, Inorg. Chim. Acta, 18, 77 (1976); https://doi.org/10.1016/S0020-1693(00)95588-9.
R.C. Mehrotra, Pure Appl. Chem., 60, 1349 (1988); https://doi.org/10.1351/pac198860081349.
D.J. Bray, J.K. Clegg, L.F. Lindoy and D. Schilter, Adv. Inorg. Chem., 59, 1 (2006); https://doi.org/10.1016/S0898-8838(06)59001-4.
G. Aromí, P. Gamez and J. Reedijk, Coord. Chem. Rev., 252, 964 (2008); https://doi.org/10.1016/j.ccr.2007.07.008.
P.A. Vigato, V. Peruzzo and S. Tamburini, Coord. Chem. Rev., 253, 1099 (2009); https://doi.org/10.1016/j.ccr.2008.07.013.
I.A. Hemmila, Applications of Fluorescence in Immunoassays, Wiley, New York (1991).
N. Sabbatini, M. Guardigli and J.M. Lehn, Coord. Chem. Rev., 123, 201 (1993); https://doi.org/10.1016/0010-8545(93)85056-A.
K.H. Reddy, P.S. Reddy and P.R. Babu, Transition Met. Chem., 25, 505 (2000); https://doi.org/10.1023/A:1007038514536.
J.D. Joshi, S. Sharma, G. Patel and J.J. Vora, Synth. React. Inorg. Met.-Org. Chem., 32, 1729 (2002); https://doi.org/10.1081/SIM-120016461.
H.M. Parekh, S.R. Mehta and M.N. Patel, Russ. J. Inorg. Chem., 51, 67 (2006); https://doi.org/10.1134/S003602360601013X.
Z.H. Abd El-Wahab, J. Coord. Chem., 61, 3284 (2008); https://doi.org/10.1080/00958970802039996.
R. Karvembu and K. Natarajan, Polyhedron, 21, 219 (2002); https://doi.org/10.1016/S0277-5387(01)00980-9.
H. Zeng, J. Xie and P.G. Schultz, Bioorg. Med. Chem. Lett., 16, 5356 (2006); https://doi.org/10.1016/j.bmcl.2006.07.094.
M.S. Ameerunisha Begum, S. Saha, A. Hussiain and A.R. Chakravarty, Indian J. Chem., 48A, 9 (2009).
N. Raman, L. Mitu, A. Sakthivel and M.S.S. Pandi, J. Iran. Chem. Soc., 6, 738 (2009); https://doi.org/10.1007/BF03246164.
J. Stary, The Solvent Extraction of Metal Chelates, MacMillan Company, New York (1964).
Y. Akama and A. Tong, J. Microchem., 53, 34 (1996); https://doi.org/10.1006/mchj.1996.0006.
L.J. Bellamy and L. Beecher, J. Chem. Soc., 0, 4487 (1954); https://doi.org/10.1039/JR9540004487.
Q.H. Chu, L.X. Gao, D.M. Wang, Y.H. Qi and M.X. Ding, Chem. J. Chin. Univ., 21, 439 (2000).
M. Sado, T. Ozawa, K. Jitsukawa and H. Einaga, Polyhedron, 14, 2985 (1995); https://doi.org/10.1016/0277-5387(95)00119-D.
Z. Chen, Y. Wu, F. Huang, D. Gu and F. Gan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 66, 1024 (2007); https://doi.org/10.1016/j.saa.2006.05.015.
D.L. Pavia, G.M. Lampman, G.A. Kriz and J.R. Vyvyan, Introduction to Spectroscopy, Cengage Learning India Pvt. Ltd., India, edn 5, p. 92 (2015).
N.G. Yernale and M.B.H. Mathada, Bioinorg. Chem. Appl., Article ID 314963 (2014); https://doi.org/10.1155/2014/314963.
K.R. Sangeetha Gowda, H.S. Bhojya Naik, B.V. Kumar, C.N. Sudhamani, H.V. Sudeep, T.R. Ravikumar Naik and G. Krishnamurthy, Spectrochim. Acta A Mol. Biomol. Spectrosc., 105, 229 (2013); https://doi.org/10.1016/j.saa.2012.12.011.
N. Raman, S. Sobha and L. Mitu, J. Saudi Chem. Soc., 17, 151 (2013); https://doi.org/10.1016/j.jscs.2011.03.003.
M. Shakir, S. Hanif, M.A. Sherwani, O. Mohammad and S.I. Al-Resayes, J. Mol. Struct., 1092, 143 (2015); https://doi.org/10.1016/j.molstruc.2015.03.012.
D. Dinesh, K. Murugan, P. Madhiyazhagan, C. Panneerselvam, P. Mahesh Kumar, M. Nicoletti, W. Jiang, G. Benelli, B. Chandramohan and U. Suresh, Parasitol. Res., 114, 1519 (2015); https://doi.org/10.1007/s00436-015-4336-z.