Synthesis and Characterization of New Schiff Bases Formed by Condensation of 2,9-Phenathroline-1,10-dialdehyde with Sulfur-Containing Amines

Abstract

Four new Schiff bases of 1,10-phenanthroline-2,9-dicarboxaldehyde with sulfur-containing amines such as 2-mercaptoaniline, S-alkyl/aryl dithiocarbazates and thiosemicarbazide have been synthesized and characterized by spectroscopic and X-ray crystallographic techniques. A comparative study of the methods of synthesis has been made using both traditional and microwave techniques. A significant reduction in reaction time has been observed when the microwave method was used. In some of the reactions, the yields also increased significantly.

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M. Arifuzzaman, M. Karim, T. Siddiquee, A. Mirza and M. Ali, "Synthesis and Characterization of New Schiff Bases Formed by Condensation of 2,9-Phenathroline-1,10-dialdehyde with Sulfur-Containing Amines," International Journal of Organic Chemistry, Vol. 3 No. 1, 2013, pp. 81-86. doi: 10.4236/ijoc.2013.31009.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] P. G. Sammes and G. Yahioglu, “1,10-Phenanthroline: A Versatile Ligand,” Chemical Society Reviews, Vol. 23, No. 5, 1994, pp. 327-334. doi:10.1039/cs9942300327
[2] J. Reedijk, “Comprehensive Coordination Chemistry,” G. Wilkinson, R. D. Dillard and J. A. McCleverty, Eds., Pergamon, Oxford, 1987, Vol. 2, p. 73.
[3] Y. Shen and B. P. Sullivan, “Versatile Preparative Route to 5-Substituted-1,10-phenanthroline Ligands via 1,10- Phenanthroline-5,6-epoxide,” Inorganic Chemistry, Vol. 34, No. 25, 1995, pp. 6235-6236. doi:10.1021/ic00129a003
[4] M. A. Akbar, M. H. Mirza, Ai. L. Tan, L. K. Wei and P. V. Bernhardt, “The Preparation and Characterization of Seven-Coordinated Tin (IV) Complexes of the 2,6-Diacetylpyridine Schiff Bases of S-Alkyl/Aryl-dithiocarbazates and the X-Ray Crystal Structure of the [Sn (dapsme)I2] Complex (Dapsme=Doubly Protonated form of the 2,6-Diacetylpyridine Schiff Bases of S-Methyldithiocarbazate),” Polyhedron, Vol. 23, No. 11, 2004, pp. 2037-2043. doi:10.1016/j.poly.2004.05.010
[5] S. Kumar, D. N. Dhar and P. N. Saxena, “Applications of Metal Complexes of Schiff Bases—A Review,” Journal of Scientific and Industrial Research, Vol. 68, No. 3, 2009, pp. 181-187.
[6] F. C. Kerbs, “Functionalization of the Hinge Region in Receptor Molecules for Explosive Detection,” Tetrahedron Letters, Vol. 44, No. 35, 2003, pp. 6643-6646. doi:10.1016/S0040-4039(03)01683-6
[7] H. Jiang, W. Sun and R. Zheng, “Synthesis and Magnetic Properties of Novel Containing 1,10-Phenanthroline Polymeric Complexes,” European Polymer Journal, Vol. 42, No. 2, 2006, pp. 425-433. doi:10.1016/j.eurpolymj.2005.07.003
[8] H.-W. Kuai, X.-C. Cheng and X.-H. Zhu, “Syntheses, Structures, and Properties of a Series of New Assembled Metal Complexes with 4-(Benzimidazol-1-ylmethyl)benzoate,” Journal of Coordination Chemistry, Vol. 66, No. 1, 2013, pp. 28-41. doi:10.1080/00958972.2012.746458
[9] M. Andruh, “Compartmental Schiff-Base Ligands—A Rich Library of Tectons in Desgning Magnetic and Luminescent Materials,” Chemical Communications, Vol. 47, No. 11, 2011, pp. 3025-3042. doi:10.1039/c0cc04506c
[10] N. S. Kozlov, G. P. Korotyshova, N. G. Rozhkova and E. I. Andreeva, “Synthesis of Fluorine-Containing Aromatic Azomethines with a Pesticidal Activity,” Vesti Akad Navuk USSR Ser Khim Navuk, Vol. 2, 1986, p. 54.
[11] J. Akther, S. Lindeman and M. R. Karim, “2,9-Bis(1,3- benzothiazol-2-yl)-1,10-phenanthroline Dichloro-Methane Disolvate,” Acta Crystallographica, Vol. 64, 2008, Article ID: 01836.
[12] S. Thiele, et al., “Modulation in Selectivity and Allosteric Properties of Small-Molecule Ligands for CC-Chemokine Receptors,” Journal of Medicinal Chemistry, Vol. 58, No. 18, 2012, pp. 8164-8177. doi:10.1021/jm301121j
[13] F. W. Lewis, et al., “Highly Efficient Separation of Actinides from Lanthanides by a Phenanthroline-Derived Bis- Triazine Ligand,” Journal of the American Chemical Society, Vol. 133, No. 33, 2011, pp. 13093-13102. doi:10.1021/ja203378m
[14] C. Musetti, et al., “Metal Ion-Mediated Assembly of Effective Phenanthroline-Based G-Quadruplex Ligands,” Dalton Transactions, Vol. 19, 2009, pp. 3657-3660. doi:10.1039/b904630p
[15] M. T. H. Tarafder, K. B. Chew, K. A. Crouse, A. M. Ali, B. M. Yamin and H. K. Fun, “Synthesis and Characterization of Cu(II), Ni(II) and Zn(II) Metal Complexes of Bidentate NS Isomeric Schiff Bases Derived from S-Methyldithiocarbazate (SMDTC): Bioactivity of the Bidentate NS Isomeric Schiff Bases, Some of Their Cu(II), Ni(II) and Zn(II) Complexes and the X-Ray Structure of the Bis[S-methyl-β-N-(2-furylmethyl) Methylenedithio-carbazato]zinc(II) Complex,” Polyhedron, Vol. 21, No. 27-28, 2002, pp. 2683-2690. doi:10.1016/S0277-5387(02)01285-8
[16] CrystalClear: Rigaku Corporation, “CrystalClear Software User’s Guide, Molecular Structure Corporation,” Rigaku Corporation, 1999, pp. 1718-1725.
[17] G. M. Sheldrick, “Program for the Solution and Refinement of Crystal Structures,” University of GÖttingen, GÖttingen, 1997.
[18] L. J. Farrugia, “WinGX Suite for Small-Molecule Single-Crystal Crystallography,” Journal of Applied Crystallography, Vol. 32, 1999, pp. 837-838. doi:10.1107/S0021889899006020

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