C 6 H 11 S -Na + (generated insitu by reaction of NaOH with C 6 H 11 SH) on treatment with 1-(2-chloroethyl) piperidine hydrochloride under N 2 atmosphere resulted in (1-(2-cyclohexyl thioethyl) piperidine) (L 1 ) as orange solid. It's complexes having the formula [ZnCl 2 . L 1 ] (1), [CdCl 2 . (L 1 )] (2) and [HgCl 2 . L 1 ] (3) have been prepared. L 1 and its complexes 1-3 were characterized on the basis of physico-chemical and spectral (FT-IR, Mass, 1 H, 13 C and DEPT 135 o NMR) studies. Powder XRD diffraction pattern reveals the crystalline nature of L 1 and complex 1. Complexes 1-3 adopt distorted tetrahedral geometry showing bidentate mode of coordination through S and N. Using DFT-based optimization of structures, the HOMO-LUMO energy gaps and molecular electrostatic potential maps (EPM) of compound L 1 and complexes 1-3 were theoretically calculated at the B3LYP/6-311G (d, p) level of theory. HOMO-LUMO energy gap was calculated which allowed the calculation of relative properties like chemical hardness, chemical inertness, chemical potential, nucleophilicity and electrophillicity index of the synthesized products. The experimentally obtained IR and NMR results showed a good correlation with those of the theoretical ones. Ligand L 1 and complexes 1-3 display significant antibacterial and antifungal activity.