Spectral, Thermal and In Vitro Antibacterial Studies on Cadmium(II)– bis(2,2/-methylidenephenol)diaminoethane

Abstract

The objective of this work is to prepare a new synthetic protocol of the cadmium(II) complex of bis(2,2’-methylylidenephenol)diaminoethane (H2BMPDE) and study the antimicrobial bioefficacy. In this work, we report the extractive method for the synthesis of cadmium(II) complex of  bis(2,2’-methylidenephenol)diaminoethane from salicylaldehyde, ethylenediamine, hydrochloric acid, and cadmium sulfate in a single, simple step. The ligand and the complex were characterized by FTIR, UV-Vis, 1H and 13C NMR, magnetic moment, GC-MS, thermal and elemental analysis. The chemical data indicated the formation of 1:1 (metal:ligand) mole ratio and distorted tetrahedral geometry was suggested as based on spectral data and magnetic moment. The results of preliminary antibacterial study revealed that Cd(II) H2BMPDE complexes prepared from different acids (HCl, HNO3, H2SO4) were effective against clinically important Gram-negative bacteria (Escherichia coli, pseudomonas, Klebsiella ) and Gram-positive bacterium (Staphylococcus aureus).The result indicated a new synthetic protocol for the synthesis of H2BMPDE complexes. On the application, H2BMPDE and its complexes could be considered as a potential antibacterial agent with further investigative analysis.

Keywords

• stability studies
• Cadmium H2BMPDE
• physicochemical studies
• antimicrobial bioefficacy

References

1. 1. Zaky RR, Yousef TA, Ibrahim KM. Co(II), Cd(II),Hg(II) and U(VI)O2 complexes of o-hydroxyacetophenone[N-(3-hydroxy-2-naphthoyl)] hydrazone: physicochemical study,thermal studies and antimicrobial activity. Spectrochim. Acta Part A. 2012 Nov; 97: 683-94.
2. 2. Zhang J A, Pan M, Zhang JY, Kang BS, Su CY. Syntheses, structures and bioactivities of cadmium(II) complexes with a tridentate heterocyclic N- and S-ligand. Inorg. Chim. Acta. 2009; 362: 3519-25.
3. 3. Naz M, Aghatabay A, Neshat T, Karabiyik M, Somer D, Haciu B D. Synthesis, characterisation and antimicrobial activity of Fe(II), Zn(II), Cd(II) and Hg(II) complexes with 2,6-bis(benzimidazol-2-yl)pyridine. Euro. J. Med.Chem. 2007; 42:205-13.
4. 4. Warad I, Ali Khan A, Azam M, Al-Resayes I, Haddad S F. Design and structural studies of diimine/CdX2 (X = Cl, I) complexes based on 2,2-dimethyl-1,3-diaminopropane ligand. J. Mol. Struct. 2014;1062: 167–73.
5. 5. Shashidhar Reddy N, Shankara B S, Murali Krishana P, Basavaraj C, Mahesh B. Synthesis, characterisation, and antibacterial activity of Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) complexes of Schiff’s base type ligands containing benzofuran moiety. J. Inorg. Chem. Article ID 614628,2013: 1-10.
6. 6. Montazerozohori M, Khani S, Tavakol H, Hojjati A, Kazemi M. Synthesis, spectroscopic and thermal studies of some IIB group complexes with a new N2-Schiff base ligand. Spectrochim. Acta Part A.2011; 81: 122-27.
7. 7. Montazerozohori M, Joohari S, Musavi S A. Synthesis and spectroscopic studies of some cadmium(II) and mercury(II) complexes. Spectrochim. Acta Part A. 2009; 73: 231-37.
8. 8. Mahmoudi G, Morsali A, Zeller M. Mercury(II) acetate/thiocyanate coordination polymers with n-donor ligands, spectroscopic, thermal and structural studies. Inorg. Chim. Acta. 2009;362: 217-25.n

9. 9. Morteza M, Masoud N, Maryam H, Asghar N, Saeedeh S. Synthesis of some new antibacterial active cadmium and mercury complexes of 4-(3-(2-(4-(dimethyl aminophenyl allylidene aminopropyl-imino)prop-1-ethyl)-N,N-dimethylbenzene amine. Chemical Speciation and Bioavailability. 2014; 26(4): 240
10. 10. Baleizao C, Garcia H. Chiral Salen Complexes: An Overview to Recoverable and Reusable Homogeneous and Heterogeneous Catalysts. Chem. Rev. 2006; 106: 3987-4043.
11. 11. Yang S, Kon H, Wang H, Chang K, Wang J. Efficient Electrolyte of N, NI-bis(salicylidene) ethylenediamine zinc(II) Iodide in Dye-sensistized Solar Cells. New. J. Chem. 2010; 34: 313-17.
12. 12. Bae HJ, Hwang KY, Lee M H, Do Y. Salen-Aluminium Complexes as Host Materials for Red Phosphorescent Organic Light Emitting Diodes. Bull. Korean. Chem. Soc. 2011;32(9): 3290-94.
13. 13. Starkie C. Advances in Carbon Capture and Storage Research. John Matthey Technol. Rev. 2015; 59(3): 182-87.
14. 14. Abou-Melha K S, Faruk H. Bimetallic Complexes of Schiff Base bis[4-hydroxy Coumarin-3-yl]–IN, 5-Nthiocarboxy drazone) as a Potentially Dibasic Pentadentate Ligand. Synthesis, Spectra and Antimicrobial Properties. J Iran. Chem Soc. 2008;5: 122-34
15. 15. Brown R, Fischer R, Blunk J, Berlin KD, Ramalingam K, Durham N N. Biological Activity and Active Groups of Novel Pyrazoles, Thiosemicarbazones and Substituted Thiazoles. Proc. Okla. Acad. Sc. 1978; 56: 15 -17.
16. 16. Biswas FB, Roy TG, Rahman MA, Mran TB .An in vitro antibacterial and antifungal effects of cadmium(II) complexes of hexamethyltetraazacyclotetradecadiene and isomers of its saturated analogue. Asian Pac J Trop Med.2014; 7S1:S534-39.
17. 17. Nworie FS, Nwabue FI. Solvent Extraction Studies of Metal Complexes Derived from a Tetradentate Schiff Base Bis(salicylidene)ethylenediamine (H2SAL) in Acid Medium. International Journal of Innovative and Applied Research. 2014; 2 (6): 66-75.
18. 18. Sreeramulu J, Jaffer Mohiddin G, Raffi MD, Mallikarjuna Rao M, Musthak Ahamad R. Synthesis, Spectral Analysis and Antimicrobial Activity of Novel Dithiocarbamate Schiff Base Metal Complexes. Archives of Applied Science Research. 2012; 4(2): 858-62.
19. 19. Schaubert K, Hufsky F, Bocker S. Computational mass spectrometry for small molecules. Journal of cheminformatics.2013; 5:12-35
20. 20. Robertson A I, Hamming M C. MASSFORM, a computer program for the assignment of elemental compositions to high resolutions mass spectra data. Biomed mass spectrum. 1977; 4(4): 203-08.
21. 21. Wade L. Infrared Spectroscopy and Mass Spectrometry. Organic chemistry. 6th Edition. Pearson prentice Hull: New Jersey USA.2006: 508-58.
22. 22. Emara AAA, Ali A M, El-Asmy AF, Ragab EM. Investigation of the Oxygen Affinity of Manganese(II), Cobalt (II) and Nickel(II) Complexes with Some Tetradentate Schiff Bases. Journal of Saudi Chemical Society.2011; 18 (6): 762-73.
23. 23. Vedanayaki S, Jayaseedan P. Synthesis, Spectroscopic and Antimicrobial Studies of Binuclear Schiff Base Complexes with N202 Donor Groups. World Journal of Pharmacy and Pharmaceutical Sciences.2014; 3(9): 504-17.
24. 24. Aranha P E, dos Santos M P, Romera S, Dockal ER. Synthesis, Characterization and Spectroscopic Studies ot Tetradentate Schiff Base Chromium(III) Complexes. Polyhedron.2006; 26:1373-82.
25. 25. Ukoha PO, Oruma US. Synthesis and Antimicrobial Studies of N, N1-bis (4-methylaminobenzylidene) ethane-1,2-diamine (DAED) and its Nickel (II) and Platinium(IV) Complexes. J. Chem.Soc-Nigeria. 2014; 39(2): 102-07.
26. 26. El-Gamel N EA, Zayed MA. Fluoroquinoline Antibiotic (Enrofloxacin) Metal Complexes. Synthesis, Spectroscopic and In vitro Antimicrobial Screening Properties.World Journal of pharmaceutical research. 2014;4(1):142-62.
27. 27. El-Gamel NEA.Co-ordination Behavior and Biopotency of Metal N, N- Salen Complexes. RSC Advances. 2012;2: 5870-76.
28. 28. Enedoh M C, Nwabueze JN. Complexes of Acetone-2-amino-4-4-thiazoleacetic acid hydrazone(ATASH) withsome M(II) sulphates and acetates(M= Ni, Cu, Co, Zn, Mn).Proceedings of the 37th Annual International Conference of Chemical Society of Nigeria.2014; 169-73.
29. 29. Gluvchinsky P, Mocler G M. Nickel (II) Complexes of Some Quadridentate Schiff Base Ligands –II. Infrared Spectra. Spectrochim. Acta A. 1977; 33: 1073-77.
30. 30. Abd-Elzar MM. Spectroscopic Characterization of some Tetradentate Schiff Bases and their Complexes with Nickel, Copper and Zinc. J. Chin. Chem. Soc. 2011;148:53.
31. 31. Percy GC, Thornton DA. N-Aryl Salicyladimine Complexes: Infrared and PMR Spectra of the Ligands and Vibrational Frequencies of their Metal(II) Chelates. Journal of Inorganic and Nuclear Chemistry.1972; 34(11):3357-67.
32. 32. Borah D, Baruah MK. Kinetic and Thermodynamic Studies on Oxidation and Desulphurization of Organic Sulphur from India Coal at 50-150oC Fuel. Processing Technology.2001;72(2):83-101
33. 33. Aghera VK, Parsania PH. Effect of Substituent’s on Thermal Behaviour of some Symmetric Double Schiff Bases Containing a Cardo group. Journal of Scientific and Industrial Research.2008; 67: 1083-87.
34. 34. Bruylant G, Wouters J, Michaux C. Differential Scanning Calorimetry in Life Science: Thermodynamics Stability, Molecular Recognition and Application in Drug Design. Current Medicinal Chemistry.2005; 12: 2011-20.
35. 35. Amadi OK, Otuokere IE, Iroka CE. Co-ordination Behaviour of 4-[(7-chloroquinolin-4-yl)amino]-2-(diethyl amino)methyl]phenol ligandTowards Fe(II),Ni(II),Co(II) and Cu(II) Metal Ions.Proceedings of 37th Annual International Conference of Chemical Society of Nigeria. 2014; 6-11.
36. 36. Wahab Z HA, Mashaly MM, Salman A, Elshetary B A, Faheim A A. Co(II), Ce (III) and UO2 (VI)bis salicylatothiosemicabazide Complexes: Binary and Ternary Complexes Thermal Studies and Antimicrobial Activity, Spectrochim. Acta. Part A.2004; 60: 2861-73.
37. 37. Pervaiz M, Yousaf M, Sagir M, Mushtaq M, Naz M Y, Ullah S, Mushtaq R. Synthesis and Characterization of Bimetallic Post Transition Complexes for Antimicrobial Activity, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry.2015; 45:546-552.