Investigation of the antioxidant and radical scavenging activities of some phenolic Schiff bases with different free radicals

The antioxidant properties of some phenolic Schiff bases in the presence of different reactive particles such as (OH)-O-center dot, (OOH)-O-center dot, (CH2=CH-O-O-center dot), and O--center dot(2) were investigated. The thermodynamic values, Delta H-BDE, Delta H-IP, and Delta H-PA, were used for this purpose. Three possible mechanisms for transfer of hydrogen atom, concerted proton-electron transfer (CPET), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were considered. These mechanisms were tested in solvents of different polarity. On the basis of the obtained results it was shown that SET-PT antioxidant mechanism can be the dominant mechanism when Schiff bases react with radical cation, while SPLET and CPET are competitive mechanisms for radical scavenging of hydroxy radical in all solvents under investigation. Examined Schiff bases react with the peroxy radicals via SPLET mechanism in polar and non-polar solvents. The superoxide radical anion reacts with these Schiff bases very slowly.