Synthesis, Characterization and Biological Activity Studies on Novel 4-Chloro-2- [(1-Phenyl-1H-Tetrazol-5-Ylimino)-Methyl] Phenol and Its Metal Complexes
Author(s)
Ranjithreddy Palreddy,
Jaheer Mohmed,
Nagula Narsimha,
Boinala Aparna,
Mariyam,
Ch. Sarala Devi*
Affiliation(s)
Department of Chemistry, University College of Science, Osmania University, Hyderabad, India.
Department of Chemistry, University College of Science, Osmania University, Hyderabad, India.
ABSTRACT
Novel 4-Chloro-2-[(1-phenyl-1H-tetrazol-5-ylimino)-methyl] phenol (Cl-PTMP) and its transition metal complexes were synthesized and characterized by FT-IR, 1H-NMR, UV-Vis spectroscopy, Mass spectrometry, TGA and SEM. The pH-metric technique was applied to get an insight of the number of dissociable protons and protonation sites in candidate compound. The pH-Metric studies were also carried out in presence of metal ions to establish the formation of corresponding metal complexes in solution. Further, the metal ligand compositions of Cu (II) and Co (II) complexes were determined spectrophotometrically by employing Job’s continuous variation method. To know the molecular properties in title imine compound suitable for metal ion coordination, the computational studies were carried out by employing HyperChem 7.5 tools. The energies of HOMO and LUMO frontier orbitals and their electron density contour maps were generated with geometry optimized molecule. Biological activity of Cl-PTMP and its metal complexes was investigated by disc diffusion method.
Novel 4-Chloro-2-[(1-phenyl-1H-tetrazol-5-ylimino)-methyl] phenol (Cl-PTMP) and its transition metal complexes were synthesized and characterized by FT-IR, 1H-NMR, UV-Vis spectroscopy, Mass spectrometry, TGA and SEM. The pH-metric technique was applied to get an insight of the number of dissociable protons and protonation sites in candidate compound. The pH-Metric studies were also carried out in presence of metal ions to establish the formation of corresponding metal complexes in solution. Further, the metal ligand compositions of Cu (II) and Co (II) complexes were determined spectrophotometrically by employing Job’s continuous variation method. To know the molecular properties in title imine compound suitable for metal ion coordination, the computational studies were carried out by employing HyperChem 7.5 tools. The energies of HOMO and LUMO frontier orbitals and their electron density contour maps were generated with geometry optimized molecule. Biological activity of Cl-PTMP and its metal complexes was investigated by disc diffusion method.
KEYWORDS
Synthesis, Cu (II) and Co (II) Complexes, pH-Metry, Spectro-Analytical and Biological Studies
Synthesis, Cu (II) and Co (II) Complexes, pH-Metry, Spectro-Analytical and Biological Studies
Cite this paper
Palreddy, R. , Mohmed, J. , Narsimha, N. , Aparna, B. , Mariyam, &. and Devi, C. (2015) Synthesis, Characterization and Biological Activity Studies on Novel 4-Chloro-2- [(1-Phenyl-1H-Tetrazol-5-Ylimino)-Methyl] Phenol and Its Metal Complexes. Journal of Materials Science and Chemical Engineering, 3, 45-59. doi: 10.4236/msce.2015.310006.
Palreddy, R. , Mohmed, J. , Narsimha, N. , Aparna, B. , Mariyam, &. and Devi, C. (2015) Synthesis, Characterization and Biological Activity Studies on Novel 4-Chloro-2- [(1-Phenyl-1H-Tetrazol-5-Ylimino)-Methyl] Phenol and Its Metal Complexes. Journal of Materials Science and Chemical Engineering, 3, 45-59. doi: 10.4236/msce.2015.310006.
References
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http://dx.doi.org/10.1007/s10593-007-0001-5 [2] Schocken, M.J., Creekmore, R.W., Theodoridis, G., Nystrom, G.J. and Robinson, R.A. (1989) Microbial Transformation of the Tetrazolinone Herbicide f5231. Applied and Environmental Microbiology, 55, 1220. [3] Butter, R.N., Katritzky, A.R. and Rees, C.W. (1984) The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds. Comprehensive Heterocyclic Chemistry, 5, 791. [4] Mavromoustakos, T., Kolocouris, A., Zervou, M., Roumelioti, P., Matsoukas, J. and Weisemann, R. (1999) An Effort to Understand the Molecular Basis of Hypertension through the Study of Conformational Analysis of Losartan and Sarmesin Using a Combination of Nuclear Magnetic Resonance Spectroscopy and Theoretical Calculations. Journal of Medicinal Chemistry, 42, 1714-1722.
http://dx.doi.org/10.1021/jm980499w [5] Mekni, N. and Bakloiti, A. (2008) Synthesis of New 1-Substituted 4-Perfluoroalkyl Tetrazol-5-Ones. Journal of Fluorine Chemistry, 129, 1073-1075.
http://dx.doi.org/10.1016/j.jfluchem.2008.06.019 [6] Burger, A. (1991) Isosterism and Bioisosterism in Drug Design. Progress in Drug Research, 37, 287. [7] Ranjithreddy, P., Jaheer, M., Narsimha, N., Srinivas, B. and Sarala Devi, Ch. (2014) Synthesis, Characterization, Biological Activity and DNA Cleavage Studies on Tetrazole Imine Base and Their Metal Complexes—An Experimental and Theoretical Approach. IOSR Journal of Pharmacy, 4, 21. [8] Broo, A. and Lincoln, P. (1997) Ab Initio and Semiempirical Calculations of Geometry and Electronic Spectra of Ruthenium Organic Complexes and Modeling of Spectroscopic Changes upon DNA Binding. Inorganic Chemistry, 36, 2544-2553.
http://dx.doi.org/10.1021/ic961193n [9] Gilpin, R.K. and Predicting, I.D. (1995) Predicting 1D NMR Spectra. Analytical Chemistry, 67, 541.
http://dx.doi.org/10.1021/ac00113a722 [10] Vanciuc, O. (1996) HyperChem Release 4.5 for Windows. Journal of Chemical Information and Computer Sciences, 36, 612.
http://dx.doi.org/10.1021/ci950190a [11] Winchester, W.R. and Doyle, M.P. (1992) Computer Software Reviews. Journal of the American Chemical Society, 114, 9243.
http://dx.doi.org/10.1021/ja00049a600 [12] Witanowski, W., Biedrzycka, Z., Sicinska, W., Grabowski, Z. and Webb, G.A. (1996) Solvent Effects on the Nitrogen NMR Shieldings in Oxazole and Oxadiazole Systems. Journal of Magnetic Resonance, Series A, 120, 148-154.
http://dx.doi.org/10.1006/jmra.1996.0112 [13] Irving, H.M. and Rossotti, H.S. (1954) The Calculation of Formation Curves of Metal Complexes from pH Titration Curves in Mixed Solvents. Journal of Chemical Society (Resumed), 2904-2910.
http://dx.doi.org/10.1039/jr9540002904 [14] Irving, H.M. and Rossetti, H.S. (1953) 680. Methods for Computing Successive Stability Constants from Experimental Formation Curves. Journal of Chemical Society (Resumed), 3397-3405.
http://dx.doi.org/10.1039/jr9530003397 [15] Irving, H.M. and Rossotti, H.S. (1956) Some Relationships among the Stabilities of Metal Complexes. Acta Chemica Scandinavica, 10, 72-93.
http://dx.doi.org/10.3891/acta.chem.scand.10-0072 [16] Laxmi, K., Bhargavi, G., Sireesha, B. and Sarala Devi, C. (2006) Interaction of 2-(2’-Hydroxy)Phenylbenzothiazoline with Some Metal Ions: Determination of Its Dissociation Constant in Aquo-Organic Media. Bulletin of the Chemical Society of Ethiopia, 20, 161-166. http://dx.doi.org/10.4314/bcse.v20i1.21156 [17] Bhargavi, G., Sireesha, B. and Sarala Devi, C. (2002) A Study on Coordination Properties of 3-Mercapto-1,2,4-Tria- zole in Solution and Characterization of Its Solid Metal Complexes. Bulletin of Pure and Applied Sciences, 21C, 1. [18] Bhargavi, G., Sireesha, B. and Sarala Devi, C. (2002) A Study on Potential Donor Sites of Some Substituted 1,2,4- Triazoles and Their Denticity. Journal of the Indian Chemical Society, 79, 826. [19] Sireesha, B., Bhargavi, G., Sita, C. and Sarala Devi, C. (2006) Interaction of 2-(2'-Hydroxy) Phenyl Benzothiazoline with Some Metal Ions: Determination of Its Dissociation Constant in Aquo-Organic Media. Bulletin of Pure and Applied Sciences, 25C, 1. [20] Aliya, Sireesha, B., Venkata Ramana Reddy, C. and Sarala Devi, C. (2008) Spectral and Equilibrium Studies on Some New Derivatives of 4-Amino-5-Phenyl-3-Mercapto-1,2,4-Triazole. Journal of the Indian Chemical Society, 85, 926- 929.