Novel imine-tethering cationic surfactants, namely (E)-3-((2-chlorobenzylidene)amino)-N-(2-(decyloxy)-2-oxoethyl)-N,N-dimethylpropan-1-aminium chloride (ICS-10) and (E)-3-((2-chlorobenzylidene)amino)-N,N-dimethyl-N-(2-oxo-2-(tetradecyloxy)ethyl)propan-1-aminium chloride (ICS-14), were synthesized, and the chemical structures were elucidated by various spectroscopic approaches. The surface properties of the target-prepared imine-tethering cationic surfactants were investigated. The effects of both synthesized imine surfactants on carbon steel corrosion in a 1.0 M HCl solution were investigated by weight loss (WL), potentiodynamic polarization (PDP), and scanning electron microscopy (SEM) methods. The outcomes show that the inhibition effectiveness rises with raising the concentration and diminishes with raising the temperature. The inhibition efficiency of 91.53 and 94.58 % were attained in the presence of the optimum concentration of 0.5 mM of ICS-10 and ICS-14, respectively. The activation energy (Ea) and heat of adsorption (Qads) were calculated and explained. Additionally, the synthesized compounds were investigated using density functional theory (DFT). Monte Carlo (MC) simulation was utilized to understand the mechanism of adsorption of inhibitors on the Fe (110) surface.