Synthesis, structures, spectral properties and DFT quantum chemical calculations of (E)-4-(((4-propylphenyl)imino)methyl)phenol and (E)-4-((2-tolylimino)methyl)phenol; their corrosion inhibition studies of mild steel in aqueous HCl

Abstract

Two Schiff base compounds with similar backbone, but different positions and lengths of alkyl groups, (E)-4-(((4-propylphenyl)imino)methyl)phenol (PMP) and (E)-4-((2-tolylimino)methyl)phenol (TMP) have been synthesized. Their structures were established by spectroscopic techniques which include FTIR, 1H and 13C NMR, relative molecular mass (mass spect.), and single crystal X-ray crystallography. The spectroscopic methods revealed the characteristic imine functional groups and the exact molecular masses of the compounds. Single crystal analysis revealed an orthorhombic crystal system with Pca21 space group for the two compounds; and the structure of PMP reveal that the propyl group is disordered over two positions in 0.79:0.21 ratio. The corrosion inhibition behaviour of the two Schiff bases were studied by electrochemical measurements. The results suggest that the two derivatives adsorbed onto the mild steel surface and formed hydrophobic films, which to an appreciable extent, protected the surface of the mild steel. Potentiodynamic polarization results strongly suggested that the investigated Schiff bases behave as mixed-type inhibitors with a more pronounced cathodic nature, and the adsorption isotherm basically obeys the Langmuir isotherm. Quantum chemical computations were also employed to provide further explanations on the adsorption mode, and the theoretical predictions conformed to the experimental results.