Sains Malaysiana 36(1): 21-26 (2007)
Synthesis and Characterization of Some Diorganotin(IV) Complexes
of 2,3-Dihydroxybenzaldehyde N(4)-Substituted Thiosemicarbazone
(Sintesis dan Pencirian Kompleks Diorganostanum(IV) dengan
N(4)- Tiosemikarbazon Terbitan 2,3-Dihidroksibenzaldehid)
Abdurazag T. Swesi, Yang Farina & Ibrahim Baba
School of Chemical Sciences and Food Technology
Faculty of Science and Technology, Universiti Kebangsaan Malaysia
ABSTRAK
Sebatian organostanum terutama terbitan dialkilstanum dilaporkan mempunyai sifat anti-tumor. Kompleks diorganostanum(IV) jenis Me2SnL1, Me2SnL2, Bu2SnL1, Bu2SnL2 dan Ph2SnL1 (L1H2 dan L2H2 adalah anion ligan tiosemikarbazon yang terbentuk daripada tindak balas kondensasi 2,3-dihidroksibenzaldehid dengan tiosemikarbazida atau penukarganti N(4)-metilnya) telah disintesis menggunakan nisbah logam kepada ligan, 1:1. Kompleks yang terhasil dicirikan secara analisis unsur dan teknik spektroskopi inframerah dan resonans magnet nukleus (1H, 13C, 119Sn). Pembentukan kompleks di antara moieti organostanum(IV) dengan anion 2,3-dihidroksibenzaldehid tiosemikarbazon dan 2,3-dihidroksibenzaldehid 4-metiltiosemikarbazon berlaku dengan pengelatan pada kedudukan o-dihidroksi. Kompleks dicadangkan mempunyai geometri tetrahedron.
Kata kunci: sintesis; organostanum; tiosemikarbazon
ABSTRACT
Organotin compounds especially the dialkyltin derivatives are reported to possess anti-tumour properties. The diorganotin(IV) complexes of the type Me2SnL1, Me2SnL2, Bu2SnL1, Bu2SnL2 and Ph2SnL1 (L1 and L2 is the anion of the thiosemicarbazone ligand formed by the condensation reaction of 2,3-dihydroxybenzaldehyde with thiosemicarbazide or its N(4)-methyl substituent) were synthesized using 1:1 metal-to-ligand reactant ratios. The newly synthesized complexes were characterized using elemental analysis, infrared and nuclear magnetic resonance (1H, 13C, 119Sn) spectroscopic techniques. Complex formation between the organotin(IV) moiety and the anions of 2,3-dihydroxybenzaldehyde thiosemicarbazone and 2,3-dihydroxybenzaldehyde 4-methylthiosemicarbazone occurred with chelation at the o-dihydroxy positions. The complexes are proposed to have tetrahedral geometry.
Keywords: synthesis; organotin; thiosemicarbazones
RUJUKAN/REFERENCES
Ackerman, A. J., Fanwick, P.E., Green, M. A., John, E., Running, W. E., Swearingan, J. K., Webb, J. W. & West, D. X. 1999. Structural and spectral studies of copper(II) and nickel(II) complexes of pyruvaldehyde mixed bis{N(4)-substituted thiosemicarbazones}. Polyhedron 18: 2759-2767.
Ashfaq, M., Khan, M. I., Baloch, M. K. & Malik, A. 2004. Biologically potent organotin(IV) complexes of 2-maleimidoacetic acid. J. Organomet. Chem. 689: 238-245.
Casas, S. J. A. Sanchez, J. Sordo and A. Vazquez-Lopez. 1994. Diorganotin(IV) derivatives of salicylaldehydethiosemicarbazone. The crystal structure of dimethyl- and diphenyl(saicylaldehydethiosemicarbazonato)tin(IV). Inorganica Chimica Acta. 216: 169-175.
Casas, S.J., Alfonso Castineias, Maria C. Rodriguez- Arguelles, Agustin Sanchez, Jose Sordo, Antonia Vazquez-Lopez and Ezequiel M. Vazquez-Lopez. 2000. Diorganotin(IV) complexes of imidazole-2-carbaldehyde thiosemicarbazone (H2ImTSC). The crystal and molecular structures of the free ligand and of [SnMe2(ImTSC)]. J.Chem. Soc., Dalton Trans. 2267-2272.
Davis AG, Smith PJ. 1982. In Comprehensive Organometallic Chemistry, Willkinson G, Stone FGA, Abel EW(eds), Pergamon: New York, Vol. 2: 519.
El-Hendawy Ahmed M., Abd El-Ghany El-Kourashy and May M. Shanab. 1992. Schiff base complexes of ruthenium(III), molybdenum and uranium(VI), and use of the former as catalytic organic oxidants. Polyhedron. 11(5): 523-530.
El-Hendawy M., W. P. Griffith, C. A. O’ Mathoey and D. J. Williams. 1989. Complexes of naphthalene2,3-diol (H2ND) with group VI and group VIII metals, and the X-ray crystal structure of cis-(NH4)2[MoO5(ND)2].2H2O. Polyhedron. 8: 519-525.
El-Hendawy M., W. P. Griffith and C. A. Pumphrey. 1988. complexes of osmium, uranium, molybdenum, and tungsten with the catechol amines adrenaline, noradrenaline, dopamine, dopa and isoproterenol. J. Chem. Soc., Dalton Trans. 1817-1821.
Farina Y. A.A., Baba, I., Othman, A. and Nor Fadzilah Othman. 1997. Jur. Sains, 5 (2): 665-669.
Gielen , M., M. Melotte, G. Atassi and R. Willem. 1989. Synthesis, characterization and antitumour activity of 7,7- di-n-butyl-dioxo-6,8-dioxa-7-stanna-spiro[3,5]nonane, a di n-butyltin(IV) analog of “paraplatin”, and a series of di-n- butyltin(IV) derivatives of mono- and disubstituted malonic acids. Tetrahedron 45: 1219-1229.
Gielen, M., P. Lelieveld, D. ve Dos and R. Willem. 1992. In vitro anti-tumour activity of organotin compounds. Metal based anti-tumour drugs 2: 29-54.
Griffith W. P., C. A. Pumpherey and T. A. Rainey. 1986. Catecholato complexes of ruthenium, iridium, rhenium, molybdenum and tungsten. J Chem. Soc., Dalton Trans. 1125-1128.
Hossain M. E, M. N. Alam, M. A. Ali, M. Nazimuddin, F. E. Smith and R. E. Hayes. 1996. The synthesis, characterization and bioactivities of some copper(II) complexes of the 2-acetylpyridine Schiff bases of s-methyl- and s-benzyldithiocarbazate, and the x-ray crystal structure of the nitrato(s-benzyl-β-n-(2-acetylpyridyl) methylenedithiocarbazato)copper(II) complex. Polyhedron, 15: 973-979.
Mabrouk, H. E. & D. G. Tuck 1988. The direct electrochemical synthesis of tin(II) derivatives of aromatic 1,2-diols, and a study of their oxidative addition reactions. J. Chem. Soc., Dalton Trans. 2539-2543.
Mahmoud M. R. and El-Haty M. T. 1980. Cobalt(II), Nickel(II), copper(II), and uranium(VI) complexes of some heterocyclic Schiff bases derived from hydroxyaromatic aldehydes and 2-aminopyridine. J. Inorg. Nucl. Chem. 42: 349-343.
Nath, M., Pokharia, S. and Yadav, R. 2001. Organotin(IV) complexes of amino acids and peptides. Coord. Chem. Rev. 215: 99-149.
Nath, M., Sharma, N. and Sharma, C. L. 1990. Di- and triphenyltin(IV) complexes of semi- and thiosemicarbazones. Synth. React. Inorg. Met-Org. Chem. 20 (5): 623-643.
Nielson, A. J. & W. P. Griffth. 1978. Complexes of osmium(IV) with catechol and substituted catechols. J. Chem. Soc., Dalton Trans. 1501-1506.
Tarafder T. M. H. , A. Asmadi, Siti M. S. Talib, A. M. Ali and K. A. Crouse 2001. Studies on coordination chemistry of a nitrogen-sulfur donor ligand with lighter and heavier metal ions and biological activities of its complexes. Transition Metal Chemistry 26: 170-174.
Yang Farina, I. Baba, A. H. Othman, N. Fadzilah and R. Mohamed 1998. Synthesis and characterization of dibutyltin(IV) complexes of substituted catechol. Pertanika J. Sci. & Technol. 6(2): 131-139.
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