University College of Science, Osmania University, Hyderabad-500 007, India E-mail : dr_saraladevich@yahoo.com Department of Chemistry, Chaitanya Bharati Institute of Technology, Gandipet, Hyderabad-500 075, India lnorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Uppa, Hyderabad-500 607, India Manuscript received 21 July 2011, revised 02 May 2012, accepted 11 July 2012 N'-[1-(2,4-Dihydroxyphenyl)ethylidene]benzohydrazide (DHPEBH) was synthesized and characterized by IR, mass, 1H NMR, 13C NMR and DEPT. The HyperChem 7.5 software was used for quantum mechanical calculations. The geometry optimization was carried out using ab initio method. The theoretical spectral data and QSAR parameters were generated with semi empirical single point PM3 method. The HOMO and LUMO frontier orbital energies were also computed for the optimized molecule. The experimental and theoretical spectral data are nearly comparable. As the title compound has potential electron donor atoms, the metal ion interaction studies were also carried out. The pH-metry studies indicated the presence of three dissociable protons in DHPEBH. The solid complexes of title compound with CuII , NiII , ColI and Mnll were synthesized and characterized by elemental analysis, mass, IR, TGA and DTA.