A dry benzene solution of the Schiff base N-(2-hydroxymethylphenyl)-3′-carboxy-2′-hydroxybenzylideneimine upon reacting with mercaptoacetic acid undergoes cyclization and forms N-(2-hydroxymethylphenyl)-C-(3′-carboxy-2′-hydroxyphenyl)thiazolidin-4-one, LH3 (I). A MeOH solution of I reacts with Co(II), Ni(II), Cd(II), Zr(OH)2(IV), and UO2(VI) ions and forms the monomeric coordination compounds, [M(LH)(MeOH)3] [where M = Co(II), Ni(II)], [M′(LH)(MeOH)] [here M′ = Cd(II), UO2(VI)] and [Zr(OH)2(LH)(MeOH)]. The coordination compounds have been characterized on the bases of elemental analyses, molar conductance, molecular weight, spectral (IR, NMR, and reflectance) studies, and magnetic susceptibility measurements. I behaves as a dibasic tridentate OOS donor ligand in these compounds. The compounds are nonelectrolytes ( = 3.8–8.9?mho?cm2?mol?1) in DMF. A tetrahedral structure for [Cd(LH)(MeOH)] and an octahedral structure for the remaining compounds are suggested. 1. Introduction The chemistry of thiazolidin-4-ones is very well documented in the literature and has been studied extensively due to their versatile biological properties [1]. Thiazolidin-4-ones, a saturated form of thiazole with carbonyl group on fourth carbon [2], have biological activities like those that are antipsychotic [3], antitubercular [4], antibacterial [5], anticonvulsant [6], antifungal [7], amoebicidal [8], antioxidant [9], antibiotic [10], and so forth. Literature survey shows that much has been reported on the syntheses and characterization [11] of a variety of thiazolidin-4-ones, but very less is known about their coordination compounds [12–14]. Metal complexes play an important role in plant and animal life due to their physicochemical and biological properties. Metal ions are involved in specific interactions with antibiotics, proteins, nucleic acids, and other biomolecules [15]. Most of the drugs have improved pharmacological properties in the form of their metal complexes. Transition metal ions play a very important role in the pharmacological action of metal-based drugs and these drugs are more effective against infectious microbes than the uncomplexed drugs [16]. These facts motivate us to explore the coordination behavior of a newly synthesized thiazolidin-4-one with some transition metal ions. In this paper, we describe the syntheses and characterization of N-(2-hydroxymethylphenyl)-C-(3′-carboxy-2′-hydroxyphenyl)thiazolidin-4-one, LH3 (I) and its coordination compounds with Co(II), Ni(II), Cd(II), Zr(OH)2(IV), and UO2(VI) ions. The structure of Schiff base and
References
[1]
M. Abhinit, M. Ghodke, and N. A. Pratima, “Exploring potential of 4-thiazolidinone: a brief review,” International Journal of Pharmacy and Pharmaceutical Sciences, no. 1, pp. 47–64, 2009.
[2]
D. A. Horton, G. T. Bourne, and M. L. Smyth, “The combinatorial synthesis of bicyclic privileged structures or privileged substructures,” Chemical Reviews, vol. 103, no. 3, pp. 893–930, 2003.
[3]
N. J. Hrib, J. G. Jurcak, and J. G. Bregna, “3[4-[1-(6-Fluorobenzo[b]thiophen-3-yl)-4-piperazinyl]butyl]-2,5,5-trimethyl-4-thiazolidinone: a new atypical antipsychotic agent for the treatment of schizophrenia,” Journal of Medicinal Chemistry, vol. 35, no. 14, pp. 2712–2715, 1992.
[4]
A. Solanki and K. Kishore, “Synthesis and antitubercular activity of some 4-thiazolidinones,” Asian Journal of Chemistry, vol. 6, no. 3, p. 177, 1994.
[5]
B. P. Choudhari and V. V. Mulwad, “Synthesis of 1-(6-methylbenzofuran-2-yl)-3-aryl/[4-(β-substitutedethoxy)phenyl]propenones as marked anti-microbial agents,” Indian Journal of Chemistry, vol. 44, p. 1074, 2005.
[6]
N. J. Gaikwad and S. B. Agrawal, “Substituted 4-thiazolidinones as anticonvulsants VII,” Indian Drugs, vol. 34, no. 9, pp. 542–543, 1997.
[7]
P. V. Patel and K. R. Desai, “Synthesis and anti-bacterial activity of new isoxazolines derivatives of 3,5-diaryl isoxazolines,” Oriental Journal of Chemistry, vol. 18, no. 3, p. 311, 2002.
[8]
N. C. Desai, B. R. Parekh, and K. A. Thaker, “Preparation of some important medicinal compounds. Thiosemicarbazones, thiadiazolines, 4-thiazolidinones and 5-arylidine derivatives as antibacterial and tuberculostatic agents,” Journal of the Indian Chemical Society, vol. 64, no. 8, pp. 491–493, 1987.
[9]
T. Kato, T. Ozaki, K. Tamura, Y. Suzuki, M. Akima, and N. Ohi, “Novel calcium antagonists with both calcium overload inhibition and antioxidant activity. 2. Structure-activity relationships of thiazolidinone derivatives,” Journal of Medicinal Chemistry, vol. 42, no. 16, pp. 3134–3146, 1999.
[10]
V. S. Ingle, A. R. Sawale, R. D. Ingle, and R. A. Mane, “Synthesis of new 4-thiazolidinones bearing potentially active heteryl moities,” Indian Journal of Chemistry B, vol. 40, no. 2, pp. 124–128, 2001.
[11]
S. B. Junne, S. S. Wadje, M. M. V. Baig, and Y. B. Vibhute, “Novel heterocyclic schiff bases, 4-thiazolidinones and 2-azetidinones possessing antibacterial and antifungal activity,” International Journal of Chemical Sciences, vol. 5, p. 2093, 2007.
[12]
D. Kumar and A. Kumar, “Syntheses, magnetic and spectral studies on the coordination compounds of the polystyrene anchored thiazolidin-4-one,” E-Journal of Chemistry, vol. 9, no. 4, pp. 2532–2539, 2012.
[13]
A. M. Rehab Al-Hasani, M. M. Sinan Al-byatti, and M. S. Sarab Al Azawi, “Synthesis, structural and biological studies of /3-(1, 3- benzothiazol-2-yl) - /4H- spiro[indole2,3-[1,3]thiazolidine]- 2,/4(1H) dion with Cr (III), Mn (II), Co (II), Ni (II), Cu (II), and Zn (II) ions,” Engineering & Technology Journal, vol. 29, no. 15, pp. 3067–3078, 2011.
[14]
D. Kumar, A. Kumar, and J. Sharma, “Physico-chemical studies on the coordination compounds of thiazolidin-4-one,” Journal of Chemistry, vol. 2013, Article ID 870325, 7 pages, 2013.
[15]
J. R. Anacona and I. Rodriguez, “Synthesis and antibacterial activity of cephalexin metal complexes,” Journal of Coordination Chemistry, vol. 57, no. 15, pp. 1263–1269, 2004.
[16]
J. R. Anacona and J. Estacio, “Synthesis and antibacterial activity of cefixime metal complexes,” Transition Metal Chemistry, vol. 31, no. 2, pp. 227–231, 2006.
[17]
J. C. Duff and E. J. Bills, “The solubility of picric acid in mixed solvents. Part II. Benzene-alcohol mixtures,” Journal Ofthe Chemical Society, pp. 881–884, 1932.
[18]
A. Syamal and D. Kumar, “Syntheses of new zirconium (IV) complexes with the tridentate Schiff bases derived from o-aminophenol and salicylaldehydes or 2-hydroxy-1-naphthaldehyde,” Indian Journal of Chemistry A, vol. 24, p. 62, 1985.
[19]
F. G. Mann and B. C. Saunders, Practical Organic Chemistry, Longmans, London, UK, 1961.
[20]
R. L. Dutta and A. Syamal, Elements of Magnetochemistry, Affiliated East-West Press, New Delhi, India, 2nd edition, 1993.
[21]
P. V. Patel and K. R. Desai, “Synthesis and anti-bacterial activity of new isoxazolines derivatives of 3,5-diaryl isoxazolines,” Oriental Journal of Chemistry, vol. 18, no. 3, p. 311, 2002.
[22]
D. C. Dash, A. Mahapatra, R. K. Mahapatra, S. Ghosh, and P. Naik, “Synthesis and characterization of dioxouranium(VI), thorium(IV), oxozirconium(IV) and oxovanadium(IV) complexes with 1,11-dihydroxy-1,4,5,7,8,11-hexaaza-2,3,9,10-tetramethyl-1,3,8,10-decatetraene-6- thione and their derivatives with chloroacetic acid,” Indian Journal of Chemistry, vol. 47A, pp. 1009–1013, 2008.
[23]
R. U. Roy and K. R. Desai, “Anticancer evaluation of azetidinone and thiazolidinone derivatives of quinolone,” International Journal of Chemical Sciences, vol. 3, no. 3, p. 529, 2005.
[24]
A. Syamal and O. P. Singhal, “New dioxouranium(VI)complexes with tridentate dibasic schiff bases containing ONO donor sets,” Transition Metal Chemistry, vol. 4, no. 3, pp. 179–182, 1979.
[25]
A. Syamal and D. Kumar, “New zirconium (IV) complexes with the ons donor triden tate schiff bases derived from salicyaldehyde or substituted salicylal dehydes and 2-aminobih anethiol,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 14, no. 3, p. 325, 1984.
[26]
D. Kumar, A. Syamal, A. Gupta, M. Rani, and P. K. Gupta, “Role of pH on the formation of the coordination compounds with the schiff base derived from 3-formylsalicylic acid and 4-amino-2,3-dimethyl-l-phenyl-3-pyrazolin-5-one,” Journal of the Indian Chemical Society, vol. 87, no. 10, pp. 1185–1197, 2010.
[27]
J. R. Anacona and C. Toledo, “Synthesis and antibacterial activity of metal complexes of ciprofloxacin,” Transition Metal Chemistry, vol. 26, no. 1-2, pp. 228–231, 2001.
[28]
D. Kumar, A. Syamal, A. Kumar, P. K. Gupta, and D. Dass, “Syntheses and characterization of coordination compounds of N-(2-mercaptoethyl)-4-(3′-carboxy-2′-hydroxyphenyl)-2-azetidinone,” Journal of the Indian Chemical Society, vol. 87, no. 4, pp. 417–423, 2010.
[29]
D. Kumar, A. Syamal, and L. K. Sharma, “Synthesis and characterization of polystyrene-anchored monobasic bidentate schiff base and its complexes with bi-, tri-, tetra- and hexavalent metal ions,” Journal of Coordination Chemistry, vol. 61, no. 11, pp. 1788–1796, 2008.
[30]
D. Kumar, P. K. Gupta, A. Kumar, D. Dass, and A. Syamal, “Syntheses, spectroscopic, and magnetic properties of polystyrene-anchored coordination compounds of tridentate ONO donor schiff base,” Journal of Coordination Chemistry, vol. 64, no. 4, pp. 590–599, 2011.
[31]
M. R. Charasia, “Cu(II), Ni(II) and Co(II) complexes of N-phenyl-benzothiazolyl thiocarbamide,” Journal of Inorganic and Nuclear Chemistry, vol. 37, no. 6, pp. 1547–1548, 1975.
[32]
J. K. Nag, S. Pal, and C. Sinha, “Synthesis and characterization of cobalt(II), nickel(II), copper(II), palladium(II) and dioxouranium(VI) complexes of the antipyrine schiff base of 3-formylsalicylic acid,” Transition Metal Chemistry, vol. 30, no. 5, pp. 523–526, 2005.
[33]
A. B. P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, The Netherlands, 2nd edition, 1984.
[34]
A. Syamal, D. Kumar, A. K. Singh, et al., “Syntheses and characterization of a chelating resin containing ONO donor tridentate Schiff Base and its coordination compounds with copper (II). nickel(II), cobalt(II), iron(III), zinc(II), cadmium(II), manganese(II), molybdenum(VI), zirconium(IV) and uranium(VI),” Indian Journal of Chemistry, vol. 41, no. 7, pp. 1385–1390, 2002.
[35]
J. E. Huheey, Inorganic Chemistry, Principles of Structure and Reactivity, Harper and Row Publishers, New York, NY, USA, 3rd edition, 1983.
[36]
F. A. Cotton, G. Wilkinson, C. A. Murillo, and M. Bochmann, Advanced Inorganic Chemistry, John Wiley, New York, NY, USA, 6th edition, 1999.