New 3-(2-methoxyphenyl)-isoxazole-carvone: synthesis, spectroscopic characterization, and prevention of carbon steel corrosion in hydrochloric acid

Abstract

A novel mono-isoxazole was synthesized from (R)-Carvone and O-methoxy-benzaldoxime, via a [3 + 2] cycloaddition reaction. The newly obtained mono-isoxazole has been fully characterized by HRMS and NMR spectroscopy.3-(2-methoxyphenyl)-isoxazole-carvone (MIC) was synthesized and studied for its anti-corrosion effect on carbon steel in 1 M HCl at 298 K. The study was carried out using weight loss, electrochemical tests and surface analysis. It was found that 3-(2-methoxyphenyl)-isoxazole-carvone (MIC) has the best inhibition performance reaching up to 94% at 1.34 mM, the polarization curves demonstrate that the investigated molecule acts as a mixed type inhibitor with a cathodic predominance.The MIC adsorbed chemically and physically on the surface of carbon steel and followed the Langmuir adsorption isotherm model. DFT method was used to investigate the global and local reactivity of our compound and also it's behaviour when complexing with one iron atom. The molecular dynamics simulation results show that MIC compound can adsorb on the iron (110) surface through the oxygen and nitrogen atoms as well as p-electrons in the Phenyl ring.