Research ArticleOpen AccessGoogle Scholar indexed
Synthesis of 5-Substituted 2, 9-Dimethyl-1,10-Phenanthroline Dialdehydes and Their Schiff Bases with Sulfur-Containing Amines
Department of Chemistry, Tennessee State University, Nashville, USA
Department of Chemistry, Tennessee State University, Nashville, USA
Department of Chemistry, Tennessee State University, Nashville, USA
Chemistry, Faculty of Science, University Brunei Darussalam, Brunei Darussalam, Sudan
Chemistry, Faculty of Science, University Brunei Darussalam, Brunei Darussalam, Sudan
- 1 Department of Chemistry, Tennessee State University, Nashville, USA
- 2 Department of Chemistry, Tennessee State University, Nashville, USA
- 3 Department of Chemistry, Tennessee State University, Nashville, USA
- 4 Chemistry, Faculty of Science, University Brunei Darussalam, Brunei Darussalam, Sudan
- 5 Chemistry, Faculty of Science, University Brunei Darussalam, Brunei Darussalam, Sudan
International Journal of Organic Chemistry·Volume 03 (2013)·Pages 214–219·Published 27 August 2013·DOI10.4236/ijoc.2013.33029
Copy link · social · email
Abstract
Eight new Schiff bases of 5-nitro and 5-bromo-substituted 1,10-phenanthroline-2,9-dicarboxaldehydes with sulfur-containing amines, thiosemicarbazide, S-alkyl/aryl dithiocarbazates and 2-mercaptoaniline have been synthesized and characterized by a variety of spectroscopic methods. The condensation reactions of the dialdehydes with the amines were carried out both in the presence and absence of conc. sulfuric acid. A significant increase in yield of the Schiff bases was observed when the reactions were carried out in the presence of sulfuric acid.
Keywords5-Nitro-110-Phenanthroline Dialdehyde5-Bromo-110-Phenanthroline DialdehydeSchiff BasesS-Alkyl/AryldithiocarbazatesThiosemicarbazide
- 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
- R. Sahu, D. S. Thakur and P. Kashyap, “Schiff Base: An Overview of Its Medicinal Chemistry Potential of New Drug Molecules,” International Journal of Pharmaceutical Science and Nanotechnology, Vol. 5, No. 3, 2012, pp. 1757-1764.
- J. P. W. Eggert, U. Lüning and C. Nather, “Synthesis and Functionalisation of 5-Substituted Neocuproine Derivatives,” European Journal of Organic Chemistry, Vol. 2005, No. 6, 2005, pp. 1107-1112. doi:10.1002/ejoc.200400635
- J. Reedijk, “Comprehensive Coordination Chemistry,” In: G. Wilkinson, R. D. Gillard and J. A. McCleverty, Eds., Comprehensive Coordination Chemistry, Pergamon, Oxford, Vol. 2, 1987, p. 73.
- M. Akbar Ali, A. H. Mirza, A. 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
- M. Arifuzzaman, M. R. Karim, T. A. Siddiquee1, A. H. Mirza and M. A. 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
- G. F. Smith and F. W. Cagl Jr., “The Improved Synthesis of 5-Nitro-1,10-Phenanthroline,” Journal Organic Chemistry, Vol. 12, No. 6, 1947, pp. 781-784. doi:10.1021/jo01170a007
- H. Astroem and R. Stroemberg, “Synthesis of New OBAN’s and Further Studies on Positioning of the Catalytic Group,” Organic & Biomolecular Chemistry, Vol. 2, No. 13, 2004, pp. 1901-1907. doi:10.1039/b403652b
- R. C. Blake II, A. R. Pavlov, M. Khosraviani, H. E. Ensley, G. E. Kiefer, H. Yu, X, Li and D. A. Blake, “Novel Monoclonal Antibodies with Specificity for Chelated Uranium(VI): Isolation and Binding Properties,” Bioconjugate Chemistry, Vol. 15, No. 5, 2004, pp. 1125-1136. doi:10.1021/bc049889p
- J. P. W. Eggert and U. Lüning, “Towards A,D-(1,10-Phenanthroline)-Bridged Calix[6]arene Dendrimers,” European Journal of Organic Chemistry, Vol. 2007, No. 36, 2007, pp. 6046-6052. doi:10.1002/ejoc.200700639