Services on Demand
Article
Indicators
Related links
-
Cited by Google
-
Similars in Google
Share
South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
S.Afr.j.chem. (Online) vol.65 Durban 2012
RESEARCH ARTICLE
Spectral and thermal characterization and antimicrobial effect of 3-(5-H/Me/Cl/NO2-1H-benzimidazol-2-yl)-benzene-1,2-diols and some transition metal complexes
Aydin TavmanI, *; A. Seher BirteksozII; Faruk OksuzomerIII
IIstanbul University, Faculty of Engineering, Department of Chemistry, 34320, Avcilar, Istanbul, Turkey
IIIstanbul University, Faculty of Pharmacy, Department of Pharmaceutical Microbiology, 34452, Beyazit, Istanbul, Turkey
IIIIstanbul University, Faculty of Engineering, Department of Chemical Engineering, 34320, Avc lar, Istanbul, Turkey
ABSTRACT
3-(5-H/Me/Cl/NO2-1H-benzimidazol-2-yl)-benzene-1,2-diols (HLX; X = 1-4) ligands and HL3 complexes with Fe(NO3)3, Cu(NO3)2, Co(NO3)2, Zn(NO3)2 have been synthesized and characterized. The structural representations of the compounds are proposed on the basis of elemental analysis, molar conductivity, TGA, mass, FT-IR, 1H- and 13C-NMR spectrometry. All of the complexes are 1:1 electrolyte and have 1:1 M:L ratio except that of Cu(II).All of the complexes present fluorescence, the Co(II) complex showing the highest fluorescence intensity and the highest emission wavelength in comparison to the other complexes. Antibacterial activities of the ligands and the complexes formed by the HL3 ligand were evaluated using the disk diffusion method against six bacteria and Candida albicans. HL1, HL2, HL3 and [Cu(HL3)(L3)(H2O)2](NO3)-H2O show considerable antimicrobial activity toward S. epidermidis and C. albicans.
Keywords: Benzimidazole, benzene-1,2-diol, metal complexes, antimicrobial activity, fluorescence spectroscopy
Full text available only in PDF format.
Acknowledgements
This work was supported by the Istanbul University Research Fund and TUBITAK (The Scientific and Technological Research Council of Turkey). COST project number: TBAG-U/185 (106T086).
References
1 T.J. Lane, I. Nakagawa, J.L. Walter and A.J. Kandathil, Inorg. Chem., 1962, 1, 267-276. [ Links ]
2 D.H. Verkhovodova, N.R. Kal'nitskii, V.I. Minkin, A.D. Garnovskii and O.A. Osipov, Zh. Neorg. Khim., 1967, 12, 3385-3387; C.A. 1968, 68, 83943n. [ Links ]
3 S.K. Gupta and L.K. Mishra, J. Inorg. Nucl. Chem., 1979 , 41, 890-891. [ Links ]
4 A. Mishra, M.P. Singh and J.P. Singh, J. Indian Chem. Soc. 1980, 57, 246-251; [ Links ] A. Mishra, V.K. Singh, J. Indian Chem. Soc. 1981, 58, 122-124; [ Links ] L.K. Mishra, J. Indian Chem. Soc. 1982, 59, 408-409. [ Links ]
5 C.G. Wahlgren, A.W. Addison, S. Burman, L.K. Thompson, E. Sinn and T.M. Rowe, Inorg. Chim. Acta 1989, 166, 59-69. [ Links ]
6 M.R. Maurya and S.A. Bhakare, J. Chem. Res., Synop. 1996, 8, 390-391; C.A. 1996, 125, 264182e. [ Links ]
7 A. Tavman and B. Ülküseven, Main Group Met. Chem. 2001, 24, 205-210; [ Links ] B. Ülküseven, A. Tavman, G. Ötük and S. Birteksöz, Folia Microbiol. 2002, 47, 481-487. [ Links ]
8 Y.-P. Tong, Acta Cryst. 2005, E61, m1595-m1597. [ Links ]
9 Y.-P. Tong and B.-H. Ye, Acta Cryst. 2004, E60, m1927-m1929. [ Links ]
10 Y. Xi, J. Li and F. Zhang, Acta Cryst. 2005, E61, m1953-m1954. [ Links ]
11 H.-Y. Bu, Y.-J. Liu, Q.-F. Liu and J.-F. Jia, Acta Cryst. 2005, E61, m1986-m1987. [ Links ]
12 Y.-H. Zhao, Z.-M. Su, Y. Wang, X.-R. Hao and K.-Z. Shao, Acta Cryst. 2006, E62, m2361-m2362. [ Links ]
13 A. Tavman, N.M. Agh-Atabay, A. Neshat, F. Gücin, B. Dülger and D. Haciu, Transit. Met. Chem. 2006, 31, 194-200. [ Links ]
14 Y.P. Tong and S.L. Zheng, J. Mol. Struct. 2007, 841, 34-40. [ Links ]
15 Q. Shi, S. Zhang, F. Chang, P. Hao and W.-H. Sun, C. R. Chimie, 2007, 10, 1200-1208. [ Links ]
16 A. Tavman, S. Ikiz, A.F. Bagcigil, Y.N. Ozgür and S. Ak, J. Serb. Chem. Soc. 2009, 74, 537-548. [ Links ]
17 A. Tavman, S. Ikiz, A.F. Bagcigil, Y.N. Ozgür and S. Ak, Turk. J. Chem. 2009, 33, 321-331. [ Links ]
18 A. Tavman, S. Ikiz, A.F. Bagcigil, Y.N. Ozgür and S. Ak, Russ. J. Inorg. Chem. 2010, 55, 215-222. [ Links ]
19 A. Tavman, I.Boz, A.S. Birteksöz and A. Cinarli, J. Coord. Chem. 2010, 63, 1398-1410. [ Links ]
20 A. Tavman, N.M. Agh-Atabay, S. Güner, F. Gucin and B. Dülger, Transit. Met. Chem. 2007, 32, 172-179. [ Links ]
21 A. Tavman, I. Boz and A.S. Birteksöz, Spectrochim. Acta 2010, A77, 199-206. [ Links ]
22 H.F. Ridley, G.W Spickett and G.M. Timmis, J. Het. Chem., 1965, 2,453-456. [ Links ]
23 Clinical and Laboratory Standards Institute (CLSI). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, Approved Standard M7-A5, Wayne, PA, 2006. [ Links ]
24 Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of yeasts, Approved Standard M27-A2, Wayne, PA, 2002. [ Links ]
25 A. Tavman, Spectrochim. Acta 2006, A63, 343-348. [ Links ]
26 M. Masoud, A.E. Ali, M.A. Shaker and M.A. Ghani, Spectrochim. Acta 2005, A61, 3102-3107. [ Links ]
27 S. Chandra, X. Sangeetika and S.D. Sharma, Spectrochim. Acta 2003, A59, 755-760. [ Links ]
28 S. Padhye and G.B. Kauffman, Coord. Chem. Rev. 1985, 63, 127-160. [ Links ]
29 A.K. El-Sawaf, D.X. West, R.M. El-Bahnasawy and F.A. El-Saied, Transit. Met. Chem., 1998, 23, 227-232. [ Links ]
30 R.K. Agarwal, D. Sharma, L. Singh and H. Agarwal, Bioinorg. Chem. Appl. 2006, 2006, 1-9. [ Links ]
31 D. Kanamori, Y. Yamada, A. Onoda, T.A. Okamora, S. Adachi, H. Yamamoto and N. Ueyama, Inorg. Chim. Acta 2005, 358, 331-338. [ Links ]
32 N. Ueyama, N. Nishikava, Y. Yamada, T. OkamuraandA. Nakamura, Inorg. Chim. Acta 1998, 283, 91-97. [ Links ]
33 V.M. Leovac, L.S. Jovanovic, VS. Cesljevic, L.J. Bjelica, VB. Arion and N.V Gerbeleu, Polyhedron 1994, 13, 3005-3014. [ Links ]
34 K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, 5th edn., John Wiley & Sons, New York, 1997. [ Links ]
35 D.Y. Kong and Y.Y. Xie, Polyhedron 2000, 19, 1527-1537. [ Links ]
36 N.E. Eltayeb, S.G. Teoh, R. Adnan, H.-K. Fun and S. Chantrapromma, Acta Cryst. 2009, E65, o3227-o3228. [ Links ]
37 A. Tavman, B. Ulküseven and N.M. Agh-Atabay, Transit. Met. Chem. 2000, 25, 324-328. [ Links ]
38 A. Mikolasch, E. Hammer, U. Jonas, K. Popowski, A. Stielow and F. Schauer, Tetrahedron 2002, 58, 7589-7593. [ Links ]
39 C. Lee, J. Kim, H. Lee, S. Lee and Y. Kho, J. Nat. Prod. 2001, 64, 659-660. [ Links ]
40 V.V. Barbakadze, E.P. Kemertelidze, I. Targamadze, K. Mulkidzhanyan, J. Kemink, A.J. J. van den Berg, K.J. Beukelman and A.I. Usov, Chem. Nat. Comp. 2005, 41, 374-377. [ Links ]
41. K.K.M. Yusuff and R. Sreekala, Thermochim. Acta, 1991, 179, 313-322. [ Links ]
42. A.A. Soliman and W. Linert, Thermochim. Acta 1999, 338, 67-75. [ Links ]
43. A.M.G. MacDonald and P. Sirichanya, Microchem. J. 1969, 14, 199-206. [ Links ]
44. C. Mukhopadhyay, S. Ghosh and R.J. Butcher, Arkivoc, 2010, 9, 75-96. [ Links ]
45. L.M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence, A.J. Blake, C. Wilson and M. Poliakoff, Green Chem. 2003, 5, 187-192. [ Links ]
46 Y.-P. Tong and Y.-W. Lin, J. Chem. Crystallogr. 2008, 38, 613-617. [ Links ]
Submitted 20 April 2011
Revised 28 May 2012
Accepted 4 June 2012
* To whom correspondence should be addressed. E-mail: atavman@istanbul.edu.tr