Research Focus:

Synthesis of Schiff Bases from 2,9-dimethyl-1,10-phenanthroline dialdehyde and sulfur-containing amines


Zinia’s Research Focus:


Recently nitrogen and sulfur-containing organic chelating agents such as the Schiff bases derived from 2,9-dimethyl-1,10-phenanthroline dialdehyde and sulfur-containing amines and their metal complexes have received considerable attention because of their important roles in synthetic and medicinal chemistry[1]. By properly designing this type of compounds and studying their structure-activity relationships, potentially useful antibacterial, antifungal and anticancer agents can also be synthesized [2]. 2,9-Dimethyl-1,10-phenanthroline and its derivatives from which 2,9-dimethyl-1,10- phenanthroline dialdehydes are prepared, are themselves important ligands for complexation with many metal ions [3]. This property has made them important in different areas like self-assembly and catalysis. It has also played a significant role in both analytical and preparative coordination chemistry as well as in the preparation of many mixed-ligand complexes [4].

Although a large number of Schiff bases containing ‘hard’ nitrogen and ‘soft’ sulfur donor atoms have been synthesized using S-alkyl/aryl dithiocarbazates and heterocyclic aldehydes and ketones, which are able to form stable complexes with a variety of metal ions [5], less work has been reported on Schiff bases formed by condensation of 1,10-phenanthroline dialdehydes with sufur- containing amines such as S-alkyl/aryl dithioicarbazates, thiosemicarbazide and aminobenzenethiol.

In view of the importance of Schiff bases derived from 1,10-phenanthroline dialdehyde and sulfur-containing amines in coordination chemistry and biology, we report here the synthesis and characterization of eight new Schiff bases formed by condensation of 5-nitro-1,10-phenanthroline- 2,9-dialdehyde and 5-bromo-1,10-phenanthroline -2,9-dialdehyde with different types of sulfur-containing amines.



“Synthesis of 5-Substituted 2, 9-Dimethyl-1,10-Phenanthroline Dialdehydes and Their Schiff bases with Sulfur-containing Amines”. Zinia Jaman *, Mohammad R. Karim**, Tasneem A. Siddiquee*, Aminul H. Mirza, Mohamad A. Ali. International Journal of Organic Chemistry, 2013, Vol 3, No. 3, Accepted

[1] Sammes, P. G.; Yahioglu, G. “1,10-Phenanthroline: A Versatile Ligand”. Chem. Soc. Rev., 1994, 327.
[2] Reedijk, J. “Comprehensive Coordination Chemistry”; Wilkinson, G., Dillard, R. D.; McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 2, p 73.  
[3] Shen, Y.; Sullivan, B. P. “Versatile Preparative Route to 5-Substituted-1,10-Phenanthroline Ligands via 1,10-Phenanthroline-5,6-Epoxide”. Inorg. Chem, 1995, 34, 6235.
[4] Akbar, M. A.; Mirza, M. H.; Tan, Ai. L.; Wei, L. K.; Bernhardt, P. V. “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, 2004, 23, 2037.

[5] Kumar, S., Dhar, D.N., Saxena, P.N., “Applications of Metal Complexes of Schiff Bases – A Review”. Journal of Scientific and Industrial research, 2009, 68, 181

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