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Synthesis, spectroscopic investigation and biological activity of metal complexes with ONO trifunctionalalized hydrazone ligand

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Abstract

MnII, FeIII, CoII, NiII, CuII, ZnII, LaIII, RuIII, HfIV, ZrIV and UVI complexes of 4-methylphenylamino acetoacetylacetone hydrazone have been synthesized and characterized by elementals analyses, i.r., u.v.–vis. spectra, magnetic moments, conductances, thermal analyses (d.t.a and t.g.a) and e.s.r measurements. The i.r. data show that, the ligand behaves as a neutral bidentate type (10), (13) and neutral tridentate type (4), (11), (12) and (21) monobasic bidentate type (7) or monobasic tridentate type (2), (3), (5), (6), (8), (14), (15), (16), (18), (19), (20) and (22) or dibasic tridentate type (5), (9) and (17) towards the metal ion. Molar conductances in DMF solution indicate that, the complexes are non-electrolytes. The e.s.r spectra of solid complexes (8) and (10) show axial type spectra with \({\hbox{g}_{\|} > \hbox{g}_{\bot} > 2.0023}\), d(x2-y2) ground state with significant covalent bond character. However, complex (12), shows an isotropic type, indicating a octahedral manganese(II) complex. Antibacterial and antifungal tests of the ligand and some of its metal complexes are also carried out and it has been observed that, the complexes are more potent bactericides and fungicides than the ligand.

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References

  1. Singh N.K. and Aggarwal R.C. (1984). Indian J. Chem. 23(A): 1011

    Google Scholar 

  2. El-Bahnasawy R.M., El-Tabl A.S., El-Shereafy E., Kashar T.I. and Issa Y.M. (1999). Polish J. Chem. 73: 1952

    Google Scholar 

  3. Martin D.F., Jamusonis G.A. and Martin B.B. (1961). J. Am. Chem. Soc. 83: 73

    Article  CAS  Google Scholar 

  4. Agrawal S.K. and Chandra R. (1985). Proc. Nat. Acad. Sci. 55(A): 11

    Google Scholar 

  5. Murukan B. and Mohanan K. (2006). Transition Met. Chem. 31: 441

    Article  CAS  Google Scholar 

  6. Pandeya S.N., Smitha S., Jyoti M. and Sridhar S.K. (2005). Acta Pharm. 55: 27

    CAS  Google Scholar 

  7. Cukurovali A., Yalmaz I. and Kirbag S. (2006). Transition Met. Chem. 31: 207

    Article  CAS  Google Scholar 

  8. Ainscough E.W., Brodie A.M., Ranford J.D. and Waters J.M. (1995). Inorg. Chem. Acta 236: 83

    Article  CAS  Google Scholar 

  9. Chan S.C., Koh L.L., Leung P.H., Ranford J.D. and Sim K.Y. (1995). Inorg. Chem. Acta. 236: 101

    Article  CAS  Google Scholar 

  10. Ainscough E.W., Brodie A.M., Dobbs A.J., Ranford J.D. and Waters J.M. (1998). Inorg. Chem. Acta. 267: 27

    Article  CAS  Google Scholar 

  11. Bacchi A., Bonardi A., Carcelli M., Mazza P., Pelagati P., Pelazzi C., Pelizzi G., Solimano C. and Zani F. (1998). J. Inorg. Biochem. 69: 101

    Article  CAS  Google Scholar 

  12. Buss J.L., Arduini E., Shephard K.C. and Ponka P. (2003). Biochem. Pharmacol. 65: 349

    Article  CAS  Google Scholar 

  13. Pandeya S.N., Siram D., Nath G. and Deelereg E. (1999). Eur. J. Pharm. Sci. 9: 25

    Article  CAS  Google Scholar 

  14. Jang Y.J., Lee U. and Koo B.K. (2005). Bull. Korean Chem. Soc. 26: 925

    Article  CAS  Google Scholar 

  15. S.A. Abou El-Enein, F.A. El-Saied, T.I. Kasher and A.H. El-Wardany, Spectrochim Acta A (2006)

  16. Gudasi K.B., Patil S.A., Vadvavi R.S., Shenoy R.V. and Nethaji M. (2006). Transition Met. Chem. 31: 586

    Article  CAS  Google Scholar 

  17. Gudasi K.B., Patel M.S., Rashmi R.S., Shenoy V., Patil S.A. and Nethaji M. (2006). Transition Met. Chem. 31: 580

    Article  CAS  Google Scholar 

  18. Maurya R.C., Verma R. and Sutradha D. (2003). Synth. React; Inorg. Met. Org. Chem. 33: 435

    Article  CAS  Google Scholar 

  19. El-Tabl A.S. and Issa R.M. (2004). J. Coord. Chem. 57: 509

    Article  CAS  Google Scholar 

  20. Chandra S. and Kamar U. (2005). Spectrochim Acta A61: 219

    Google Scholar 

  21. El-Tabl A.S. (1997). Transition Met. Chem. 22: 400

    Article  CAS  Google Scholar 

  22. El-Tabl A.S., Kasher T.I., El-Bahnaswy R.M. and Ibrahim A.E. (1999). Polish J. Chem. 73: 245

    CAS  Google Scholar 

  23. Sonboti-El A. (1991). Transition Met.Chem. 16: 45

    Article  Google Scholar 

  24. Singh K., Singh R.V. and Tandon J.P. (1988). Polyhedron 7: 151

    Article  CAS  Google Scholar 

  25. El-Boraey H.A. and El-Tabl A.S. (2003). Polish J. Chem. 77: 1759

    CAS  Google Scholar 

  26. Mishra L., Jha A. and Yadaw A.K. (1997). Transition Met. Chem. 22: 406

    Article  CAS  Google Scholar 

  27. El-Tabl A.S., El-Baradie K. and Issa R.M. (2003). J. Coord. Chem. 56: 1113

    Article  CAS  Google Scholar 

  28. Hegazy W.H. (2001). Monatsh. Chem. 132: 639

    CAS  Google Scholar 

  29. Raman N., Kulandaisamy A., Thangaraja C., Manisankar P., Swanathan S.V and Vedhi C. (2004). Transition Met. Chem. 29: 129

    Article  CAS  Google Scholar 

  30. El-Tabl A.S. (2002). Transition Met. Chem. 27: 166

    Article  CAS  Google Scholar 

  31. Athappan P. and Rajagopal G. (1997). Transition Met. Chem. 22: 84

    Article  CAS  Google Scholar 

  32. Lewis L. and Wilkins R.G. (1960). Modern Coordination Chemistry. Interscience, New York, 403

    Google Scholar 

  33. El-Tabl A.S. (2002). J. Chem. Res.-s: 529

  34. Robenson S.D. and Uttly M.F. (1973). J. Chem. Soc. : 1912

  35. Nakatamato K. (1967). Infrared Spectra of Inorganic and Coordination Compounds. Wiley Inc., New York

    Google Scholar 

  36. Ma M.S. and Angelici R.J. (1980). Inorg. Chem. 19: 363

    Article  CAS  Google Scholar 

  37. El-Tabl H.M., El-Said F.A. and Ayad M.I. (2005). Synth. React. Inorg. Met.- Org. & Nano-Met. Chem. 35: 243

    Google Scholar 

  38. Raman N., Pitchaikani Y. and Kulandaisamy A. (2001). Proc. Indian Acat. Sci. (Chem. Sci.) 133: 183

    Google Scholar 

  39. Lal R.A. and Kumar A. (1999). Indian J. Chem. 38: 839

    Google Scholar 

  40. El-Motaleb A., Ramadan M., Sawodny W., El-Baradie H.F. and Gaber M. (1997). Transition Met. Chem. 22: 211

    Article  Google Scholar 

  41. El-Sawaf A.K., West D.X., El-Saied F.A. and El-Bahnasawy R.M. (1997). Synth. React. Inorg. Met. Org. Chem. 27: 1127

    Article  CAS  Google Scholar 

  42. Goodgame M., Goodgame D.M.L. and Cotton F.A. (1961). J. Am. Chem. Soc. 83: 4161

    Article  CAS  Google Scholar 

  43. Nag J.K., Pal S. and Sinha C. (2005). Transition Met. Chem 30: 523

    Article  CAS  Google Scholar 

  44. El-Tabl A.S. and Ayad M.I. (2003). Synth. React. Inorg. Met. -Org. Chem. 33: 369

    Article  CAS  Google Scholar 

  45. Thakkar N.V. and Bootwala S.Z. (1995). Indian J. Chem 34A: 370

    CAS  Google Scholar 

  46. D.N. Sathyanarayana, Electronic Absorption Spectroscopy and Related Techniques, Orient Longman Limited © Universities press(India) Limited (2001).

  47. El-Tabl A.S. and El-Enein S.A. (2004). J. Coord. Chem 57: 281

    Article  CAS  Google Scholar 

  48. Chiumia G.C., Phillips D.J. and Rae A.D. (1995). Inorg. Chim. Acta 238: 197

    Article  CAS  Google Scholar 

  49. Mayadevi S. and Yusuff K.K.M. (1997). Synth. React. Inorg. Met.-Org. Chem. 27: 319

    Article  CAS  Google Scholar 

  50. Cukurovali A., Yalmaz I. and Kirbag S. (2006). Transition Met. Chem. 31: 207

    Article  CAS  Google Scholar 

  51. Mukherjee G., Pal S., Poddar S.N. and Dey K. (1991). Indian J. Chem. 30: 952

    Google Scholar 

  52. Krishna C.H., Mahapatra C.M. and Dush K.C. (1977). J. Inorg. Nucl. Chem. 39: 1253

    Article  Google Scholar 

  53. Ravindar V., Swamy S.J., Srihari S.S. and Longaiah P. (1985). Polyhedron 4: 1511

    Article  CAS  Google Scholar 

  54. Atkins R., Brewer G., Kokot E., Mockier G.M. and Sinn E. (1985). Inorg. Chem. 24: 127

    Article  CAS  Google Scholar 

  55. Sallam S.A., Orabi A.S., El-Shetary B.A. and Lentz A. (2002). Trans. Met. Chem. 27: 447

    Article  CAS  Google Scholar 

  56. Parihari R.K., Patel R.K. and Patel R.N. (2000). J. Ind. Chem. Soc. 77: 339

    CAS  Google Scholar 

  57. Singh N.K. and Singh S.B. (2001). Transition Met. Chem. 26: 487

    Article  CAS  Google Scholar 

  58. Natarajan K., Podder R.K. and Agar Wala U. (1977). J. Inorg. Nucl. Chem. 39: 431

    Article  CAS  Google Scholar 

  59. Medhi O.K. and Agarwala U. (1980). J. Inorg. Nucl. Chem. 42: 1413

    Article  CAS  Google Scholar 

  60. Nehru K., Athappan P. and Rajagopal G. (2001). Transition Met. Chem. 26: 652

    Article  CAS  Google Scholar 

  61. El-Tabl A.S., Issa R.M. and Morsi M.A. (2004). Transition Met. Chem. 29: 543

    Article  CAS  Google Scholar 

  62. Knör G. and Strasser A. (2005). Inorg. Chem. Comm. 8: 471

    Article  CAS  Google Scholar 

  63. Wang B.D., Yang Z.Y., Wang Q., Cai T.K. and Crewdson P. (2006). Bioorg. Med. Chem. 14: 1880

    Article  CAS  Google Scholar 

  64. EL-tabl A.S. (2004). Bull. Korean Chem. Soc 25: 1

    Google Scholar 

  65. Hathaway B.J. and Billing D.E. (1970). Coord. Chem. Rev. 5: 143

    Article  CAS  Google Scholar 

  66. EL-Tabl A.S. (1996). Transition Met. Chem. 21: 428

    Article  CAS  Google Scholar 

  67. EL-Tabl A.S. (1998). Transition Met. Chem. 23: 63

    Article  CAS  Google Scholar 

  68. Procter I.M., Hathaway B.J. and Nicholls P.N. (1969). J. Chem. Soc. A : 1678

  69. A.S. EL-Tabl, Ph. D. Thesis, Menoufia University, Egypt, 1993.

  70. Tomlinson A.G. and Hathaway B.J. (1968). J. Chem. Soc. A 1685: 1905

    Article  Google Scholar 

  71. Kivelson D. and Neiman R. (1961). J. Chem. Phys. 35: 149

    Article  CAS  Google Scholar 

  72. Ray R.K. (1990). Inorg. Chem. Acta 174: 237

    Article  CAS  Google Scholar 

  73. Ray R.K. (1990). Inorg. Chem. Acta 174: 257

    Article  CAS  Google Scholar 

  74. Assour J.M. (1965). J. Chem. Phys. 43: 2477

    Article  CAS  Google Scholar 

  75. S.E. Harrison and J.M. Assour, J. Chem. Phys., 40, 365, 149 (1961).

  76. Mao Z.W., Yu K.B., Chen D., Han S.Y., Sui Y.X. and Tang W.X. (1993). Inorg. Chem. 32: 2140

    Article  Google Scholar 

  77. Bhabbhade M.M. and Srinivas D. (1993). Inorg. Chem. 32: 5458

    Article  Google Scholar 

  78. El-Tabl A.S. and Imam S.M. (1997). Transition Met. Chem. 22: 259

    Article  CAS  Google Scholar 

  79. Gaber M. and Ayad M.M. (1991). Thermochim. Acta 176: 21

    Article  CAS  Google Scholar 

  80. Thimmaiah K.N., Lioyd W.D. and Chandrappa G.T. (1985). Inorg. Chim. Acta 106: 81

    Article  CAS  Google Scholar 

  81. Franklin T.J. and Snow G.A. (1971). Biochemistry of Antimicrobial Action. 2nd edn., Chapman and Hall, London

    Google Scholar 

  82. Jadon S.C.S., Gupta N. and Singh R.V. (1995). Indian J. Chem. 34: 733

    Google Scholar 

  83. Collins C.H. and Lyn P.M. (1970). Microbial Methods. University Park Press, Baltimore

    Google Scholar 

  84. Kurtoġlu M., Ispir E., Kurtoġlu N., Toroġlu S. and Serin S. (2005). Transition Met. Chem. 30: 765

    Article  CAS  Google Scholar 

  85. Sengupta S.K., Pandey O.P., Srivastava B.K. and Sharma V.K. (1998). Transition Met. Chem. 23: 349

    Article  CAS  Google Scholar 

  86. Kurtoġlu M., Daġdelen M.M. and Toroġlu S. (2006). Transition Met. Chem. 31: 382

    Article  CAS  Google Scholar 

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EL-Tabl, A.S., EL-Saied, F.A. & AL-Hakimi, A.N. Synthesis, spectroscopic investigation and biological activity of metal complexes with ONO trifunctionalalized hydrazone ligand. Transition Met Chem 32, 689–701 (2007). https://doi.org/10.1007/s11243-007-0228-0

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