In the present work, two novel diamine-based benzyl dine were synthesized via a simple reaction. The structures of the resulting (1E,1'E)-N,N'-(ethane-1,2-diyl)bis(1-(4-(methylthio)phenyl)methanimine) (I) and (1E,1'E)-N,N'-(ethane-1,2-diyl)bis(1-(4-ethoxyphenyl)methanimine) (II) were established with the help of spectral-analytical techniques like; FTIR, ¹H, and ¹³C NMR spectrometry. The compounds were further characterized by antibacterial with different pathogens. Compounds I and II were analyzed using Density Functional Theory (DFT) through the B3LYP method with 6-31G (d, p), as basis sets to determine HOMO-LUMO, Mulliken atomic charges, and molecular electrostatic potential (MEP) of compounds. The reactivity descriptors of B3LYP (EHOMO, ELUMO,) were calculated to predict the stability of newly synthesized compounds. The MEP analysis revealed that electronegative elements in the structure possess the maximum electronic cloud. The distributions of the various atoms were probed by Mulliken population analysis. The microbiological activity of the compounds was tested on several Gram-positive bacteria.