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Preparation, Characterization and Biological Activity of New Tridentate Imine-Oxime Ligand (H2L) and Its Metal Complexes
Corresponding Author(s) : Basim H. Al-Zaidi
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
The new tridentate Schiff-oxime ligand 1-[2-(2,4-dihydroxybenzylidene)aminophenyl]ethanone oxime (H2L), prepared via condensation of equal amounts of 1-(2-aminophenyl)ethanone oxime and 4-hydroxysalicylaldehyde. H2L ligand characterized by using FTIR, UV-visible spectroscopies, 1H NMR, 13C NMR spectra and Mass spectrum. Metal ions complexes with Cr3+, Mn2+, Co2+, Ni2+ and Cu2+ ions, prepared in a M:L (1:2) ratio and characterized by IR, UV-visible spectroscopies, magnetic susceptibility, molar conductivity and flame atomic absorption measurements. Results of spectral studies proved the chelation behaviour of this ligand, which coordinated to metal ions as a monobasic NNO tridentate ligand, via imine and oxime nitrogen atoms in addition to phenolic oxygen atom, after losing its proton. The proposed geometry of all the prepared complexes was octahedral. The minimal inhibition zone against two Gram-positive (Staphylococcus aureus and Staphylococcus epidermidis) and two Gram-negative bacteria (E. coli and Klebsella spp.) also determined.
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- D. Basu, S. Mazumder, J. Niklas, H. Baydoun, D. Wanniarachchi, X. Shi, R.J. Staples, O. Poluektov, H.B. Schlegel and C.N. Verani, Chem. Sci., 7, 3264 (2016); https://doi.org/10.1039/C5SC04214C.
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- Y. Kaya, V.T. Yilmaz and O. Buyukgungor, Molecules, 21, 52 (2016); https://doi.org/10.3390/molecules21010052.
- P. Jayaseelan, S. Prasad, S. Vedanayaki and R. Rajavel, Eur. J. Chem., 2, 480 (2011); https://doi.org/10.5155/eurjchem.2.4.480-484.353.
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- R.B. Sumathi and M.B. Halli, Bioinorg. Chem. Appl., 2014, 1 (2014); https://doi.org/10.1155/2014/942162.
- G. Grabmann, S.M. Meier, Y.Y. Scaffidi-Domianello, M. Galanski, B.K. Keppler and C.G. Hartinger, J. Chromatogr. A, 1267, 156 (2012); https://doi.org/10.1016/j.chroma.2012.07.062.
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- A.M. El-Hendawy, A.M. Fayed and M.R. Mostafa, Transition Met. Chem., 36, 351 (2011); https://doi.org/10.1007/s11243-011-9477-z.
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- Babahan, E. P. Coban and H. Biyik, Maejo Int. J. Sci. Technol.,7, 26 (2013).
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- G.L. Miessler, P.J. Fischer and D.A. Tarr, Inorganic Chemistry, Pearson Education, edn 5, (2014).
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- K. Serbest, I. Degirmencioglu, S. Karabocek and S. Guner, Transition Met. Chem., 26, 232 (2001); https://doi.org/10.1023/A:1007161632102.
- S. Akine and T. Nabeshima, Inorg. Chem., 44, 1205 (2005); https://doi.org/10.1021/ic048347g.
- M. Kalita, T. Bhattacharjee, P. Gogoi, P. Barman, R.D. Kalita, B. Sarma and S. Karmakar, Polyhedron, 60, 47 (2013); https://doi.org/10.1016/j.poly.2013.04.062.
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- U. Ram Ambhure and R. Sunil, Modern Org. Chem. Res., 2, 1 (2017).
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References
D. Basu, S. Mazumder, J. Niklas, H. Baydoun, D. Wanniarachchi, X. Shi, R.J. Staples, O. Poluektov, H.B. Schlegel and C.N. Verani, Chem. Sci., 7, 3264 (2016); https://doi.org/10.1039/C5SC04214C.
B. Dede, E. Cicek and F. Karipcin, Acta Phys. Pol., 2, 203 (2016); https://doi.org/10.12693/APhysPolA.129.203.
Y. Kaya, V.T. Yilmaz and O. Buyukgungor, Molecules, 21, 52 (2016); https://doi.org/10.3390/molecules21010052.
P. Jayaseelan, S. Prasad, S. Vedanayaki and R. Rajavel, Eur. J. Chem., 2, 480 (2011); https://doi.org/10.5155/eurjchem.2.4.480-484.353.
S. El-Tabl, M. M. Abd El-wahed, S. E. Abd-El Razek, A. M. Dabrowska and S. M. El- Gamasy, Asian J. Sci. Technol., 7, 3167 (2016).
R.B. Sumathi and M.B. Halli, Bioinorg. Chem. Appl., 2014, 1 (2014); https://doi.org/10.1155/2014/942162.
G. Grabmann, S.M. Meier, Y.Y. Scaffidi-Domianello, M. Galanski, B.K. Keppler and C.G. Hartinger, J. Chromatogr. A, 1267, 156 (2012); https://doi.org/10.1016/j.chroma.2012.07.062.
P. Rafighi, M.R. Yaftian and N. Noshiranzadeh, Sep. Purif. Technol., 75, 32 (2010); https://doi.org/10.1016/j.seppur.2010.07.006.
B.N. Kumar, S.H. Kumar, G.G. Redhi and N.V.V. Jyothi, Asian J. Chem., 28, 1861 (2016); https://doi.org/10.14233/ajchem.2016.19916.
A.M. El-Hendawy, A.M. Fayed and M.R. Mostafa, Transition Met. Chem., 36, 351 (2011); https://doi.org/10.1007/s11243-011-9477-z.
E. Canpolat and M. Kaya, Pol. J. Chem., 79, 959 (2005).
S. Subbaiyan, A. Ganesan and J. Chinnasamy, J. Serb. Chem. Soc., 79, 151 (2014); https://doi.org/10.2298/JSC121201073S.
Babahan, E. P. Coban and H. Biyik, Maejo Int. J. Sci. Technol.,7, 26 (2013).
M. Ghorbanloo, M. Jaworska, P. Paluch, G.-D. Li and L.-J. Zhou, Transition Met. Chem., 38, 511 (2013); https://doi.org/10.1007/s11243-013-9718-4.
A. El-Fatah M. Ouf, M.S. Ali, M.S. Soliman, A.M. El-Defrawy and S.I. Mostafa, J. Korean Chem. Soc., 54, 402 (2010); https://doi.org/10.5012/jkcs.2010.54.4.402.
E. Pahontu, D. Ilies, S. Shova, C. Paraschivescu, M. Badea, A. Gulea and T. Rosu, Molecules, 20, 5771 (2015); https://doi.org/10.3390/molecules20045771.
R.R. Badekar, R.S. Lokhande, S.W. Kulkarni and R.M. Patil, Int. J. Adv. Res., 4, 796 (2016); https://doi.org/10.21474/IJAR01/1276.
K. Mohammadi and M. Rastegari, Spectrochim. Acta A Mol. Biomol. Spectrosc., 97, 711 (2012); https://doi.org/10.1016/j.saa.2012.07.062.
M.N. Yarasir, M. Kandaz, A. Akyildiz, K. Karadeniz, F. Dumludag and A. Koca, Monatsh. Chem., 144, 951 (2013); https://doi.org/10.1007/s00706-012-0913-3.
N. Turan, H. Körkoca, R. Adigüzel, N. Çolak and K. Buldurun, Molecules, 20, 9309 (2015); https://doi.org/10.3390/molecules20059309.
S. El-Tabl, M.M.Abd El-wahed, S.E. Abd-El Razek, S.M. El Gamasy and E.A. Mohamed, Asian J. Sci. Technol., 7, 3529 (2016).
G.L. Miessler, P.J. Fischer and D.A. Tarr, Inorganic Chemistry, Pearson Education, edn 5, (2014).
P.E. Aranha, M.P. dos Santos, S. Romera and E.R. Dockal, Polyhedron, 26, 1373 (2007); https://doi.org/10.1016/j.poly.2006.11.005.
K. Serbest, I. Degirmencioglu, S. Karabocek and S. Guner, Transition Met. Chem., 26, 232 (2001); https://doi.org/10.1023/A:1007161632102.
S. Akine and T. Nabeshima, Inorg. Chem., 44, 1205 (2005); https://doi.org/10.1021/ic048347g.
M. Kalita, T. Bhattacharjee, P. Gogoi, P. Barman, R.D. Kalita, B. Sarma and S. Karmakar, Polyhedron, 60, 47 (2013); https://doi.org/10.1016/j.poly.2013.04.062.
K.S. Patel, J.C. Patel, H.R. Dholariya, V.K. Patel and K.D. Patel, Open J. Met., 2, 49 (2012); https://doi.org/10.4236/ojmetal.2012.23008.
D. Sakthilatha and R. Rajavel, J. Chem. Pharm. Res., 1, 57 (2013).
S.A. Kettle, Coordination Compounds, Thomas Nelson and Sons, London, p. 3, 186, 212 (1975).
U. Ram Ambhure and R. Sunil, Modern Org. Chem. Res., 2, 1 (2017).
N. Gayathri and M.S. Suresh, Asian J. Chem., 29, 541 (2017); https://doi.org/10.14233/ajchem.2017.20227.