Schiff bases have been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties. The biocidal effect of Schiff bases as well as its metal complexes is of interest due to their pharmacological activities. The azomethine linkage in Schiff bases is responsible for the biological activities .A class of ligands with more than one independent chelating sequence substituted on a single phenyl function exemplify bis – chelating ligands which can bind two metal ions simultaneously and form polynuclear complexes. The concept of bis- denticity becomes interesting to study if a variety of symmetric and unsymmetric bis-chelating systems are developed and employed in the formation of metal complexes. Biologically active Schiff base has been synthesized from 2,4-dihydroxy -5-acetylacetophenone and 2- aminothiophenol and characterized by IR, NMR and electronic spectral studies. The Schiff base geometry was evaluated using molecular calculation with argus lab software . The molecule is built and geometry optimization was done using molecular mechanics uniform force field (UFF) method. Molecular orbital calculations were performed with quantum mechanics based AM1 (Austin Model 1) approximation, for the synthesized ligand. The Schiff base functions as a binucleating, multidentate chelating agent and can coordinate via the deprotonated phenolic oxygen, azomethine nitrogen and sulphur atoms to the metal ion leading to two dimensional Schiff base polymers. The ligand has been evaluated for their antimicrobial potency, where the compound exhibited moderate to good potency.