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This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Spectral, Thermal and Biological Studies of Some Metal Complexes Derived from Heterocyclic Mono Azo Dye Ligand 2'[(2'-Hydroxy-4-methyl phenyl)azo]imidazole
Corresponding Author(s) : Khalid J. Al-Adilee
Asian Journal of Chemistry,
Vol. 30 No. 2 (2018): Vol 30 Issue 2
Abstract
A new hetrocyclic mono azo dye ligand 2'[2'-(1-hydroxy-4-methyl phenyl)azo]imidazole (HMePAI) was prepared by reaction between diazonium chloride salt solution of 2'-amino-4-methyl phenol with imidazole in alkaline ethanolic solution. Nine metal complexes with Cr(III), Mn(II), Fe(III), Co(III), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) ions were prepared and characterized by analytical and spectral techniques like elemental analysis (CHN), metal contents, molar conductance, magnetic moments, 1H NMR, Mass spectra, infrared, electronic spectral, XRD spectra, SEM and thermal studies (TGA & DSC). The results indicated that the ligand (HMePAI) behaves as a tridentate in case of 1:2 [metal:ligand] complexes. Investigation of the stereochemistry of metal complexes have octahedral geometry. Biological activity of ligand (HMePAI) and its metal complexes against two types of bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative) by agar plate different technique. The biological activity was also conducted by cells viability and cytotoxicity assay on ligand and Ni(II) complex by using the lines of cancerous liver cells of the type HEPG2 and compared with line of the ordinary cells.
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References
P.M. Savanor, S.K. Bhat and R.N. Tantry, Res. J. Chem. Sci., 3, 38 (2013).
A. Khosravi, S. Moradian, K. Gharaning and F.A. Taromi Dyes Pigments, 69, 79 (2006); https://doi.org/10.1016/j.dyepig.2005.02.007.
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K.J. Al-Adilee and H.K. Dakhil, J. Al-Qadisiya Pure Sci., 16, 94 (2011).
K. Komatsu and N. Kuroki, J. Soc. Chem. Ind. Jpn., 73, 2190 (1970); https://doi.org/10.1246/nikkashi1898.73.10_2190.
M. Hranjec, K. Starcevic, S.K. Pavelic, P. Lucin, K. Pavelic and G.K. Zamola, Eur. J. Med. Chem., 46, 2274 (2011); https://doi.org/10.1016/j.ejmech.2011.03.008.
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G.M. Malik and S.K. Zadafiya, Der Chem. Sinica, 1, 15 (2010).
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K.J. Al-Adilee, Res. J. Pharm. Bio. Chem. Sci., 6, 1297 (2015).
K.J. Al-Adilee, K.A. Abedalrazaq and Z.M. Al-Hamdiny, Asian J. Chem., 25, 10475 (2013); https://doi.org/10.14233/ajchem.2013.15735.
K.J. Al-Adilee and D.Y. Fanfon, J. Chem. Chem. Eng., 6, 1016 (2012); https://doi.org/10.17265/1934-7375/2012.11.011.
J.Z. Mohammed, H. Abbas and A.A.M. Ali, Int. J. Curr. Res., 5, 3705 (2013).
H. Irving and R.J.P. Williams, J. Chem. Soc., 3192 (1953); https://doi.org/10.1039/jr9530003192.
K.J. Al-Adilee, Iraqi Nat. J. Chem. J. Chem., 28, 585 (2007).
M.B. Halli, K. Mallikarjun and S. Sadusuryakant, J. Chem. Pharm. Res., 7, 1797 (2015).
K.J. Al-Adilee and H.A.K. Kyhoiesh, J. Mol. Struct., 1137, 160 (2017); https://doi.org/10.1016/j.molstruc.2017.01.054.
M. Ozkutuk, E. Ipek, B. Aydiner, S. Mamas and Z. Seferoglu, J. Mol. Struct., 1108, 521 (2016); https://doi.org/10.1016/j.molstruc.2015.12.032.
K.J. Al-Adilee and B.A. Hatam, J. Adv. Chem., 3, 3412 (2015).
A.A. El-Bindary, G.G. Mohamed, A.Z. El-Sonbati, M.A. Diab, W.M.I. Hassan, Sh.M. Morgan and A.K.Elkholy, J. Mol. Liq., 218, 138 (2016); https://doi.org/10.1016/j.molliq.2016.02.021.
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Y. Yildiz, M.K. M. Keles, A.K. A. Kaya and S.D. S. Dincer, Chem. Sci. Trans., 2, 547 (2013); https://doi.org/10.7598/cst2013.353.
S. Saha, T. Majumdar and Mahapatra, Transition Met. Chem, 31, 1017 (2006); https://doi.org/10.1007/s11243-006-0101-6.
S. Chandra, M. Tyagi and K. Sharma, J. Iran. Chem. Soc., 6, 310 (2009); https://doi.org/10.1007/BF03245839.
L. Mangsup, S. Siripaisarnpipat and N. Chaichit,Anal. Sci., 19, 1345 (2003); https://doi.org/10.2116/analsci.19.1345.
K. Dey and K.K. Nandi, Indian J. Chem., 35A, 766 (1996).
J. C. Bailer, H. Emeleus and R. Nypholm, Comprehensive Inorganic Chemistry, Pergamon Press (1973).
S. Rao and K.H. Reddy, Indian J. Chem., 35A, 681 (1996).
T.K. Pal and C. Sinha, Proc. Indiana Acad. Sci., 113, 173 (2001); https://doi.org/10.1007/BF02704067.
O. Yamauchi, Talanta, 15, 177 (1968); https://doi.org/10.1016/0039-9140(68)80220-6.
B.B. Mahapatra and S.K. Pujari, Transition Met. Chem., 8, 202 (1983); https://doi.org/10.1007/BF00620688.
C.J. Ballhausen, Introduction to Ligand Field Theory, McGraw-Hill, New York (1962).
M. Kurahashi, Bull. Chem. Soc. Jpn., 47, 2067 (1974); https://doi.org/10.1246/bcsj.47.2067.
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M. Arshad, Saeed-ur-Rehman, A.H. Qureshi, K. Masud, M. Arif, A. Saeed and R. Ahmed, Turk. J. Chem., 32, 593 (2008).
E.T.G. Cavalheiro, F.C.D. Lemos, J.Z. Schpector and E.R. Dockal, Thermochim. Acta, 370, 129 (2001); https://doi.org/10.1016/S0040-6031(00)00777-2.
I. Kolthoff, Treatise of Analytical Chemistry, Interscience, New York, Part I, pp 745 (1959).
Powder Diffraction file, Inorganic, Published by the Joint Committee on Powder Diffraction Standard, vol. 1,No. PDIS 10Irb:662 (1967).
V.S. Gavhane, A.S. Rajbhoj and S.T. Gaikwad, Pharmachem., 8, 275 (2016).
R.M.A.Q. Jamhour, Can. Chem. Trans., 2, 306 (2014); https://doi.org/10.13179/canchemtrans.2014.02.03.0111.
M.I. Abou-Dobara, A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary and S.M. Morgan, J. Microb. Biochem. Technol., S3, 06 (2014); https://doi.org/10.4172/1948-5948.S3-006.
M. Montazerozohori, S.M. Jahromi and A. Naghiha, J. Ind. Eng. Chem., 22, 248 (2014); https://doi.org/10.1016/j.jiec.2014.07.017.
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.
E. Jawetz, J.L. Melnick and E.A. Adelbrerg, Medical Microbiology, McGraw Hill, USA, edn 24 (2007).
F. Bellina, S. Cauteruccio,A. Di Fiore and R. Rossi, Eur. J. Org. Chem., 2008, 5436 (2008); https://doi.org/10.1002/ejoc.200800738.
F. Li, J. Cui, L. Guo, X. Qian, W. Ren, K. Wang and F. Liu, Bioorg. Med. Chem., 15, 5114 (2007); https://doi.org/10.1016/j.bmc.2007.05.032.