Effect of α-tocopherol and its sulfur-containing analogs on radiation-induced chemical transformations of hexane and ethanol

A series of sulfur-containing structural analogs of α-tocopherol was synthesized, and their effect on the formation of molecular products of ethanol and hexane radiolysis under aerated and deaerated conditions was studied. The O-H bond dissociation enthalpies (BDEs) were calculated for the compounds containing hydroxyl groups. It was found that α-tocopherol and its analogs have the most significant effect on the radiolysis of ethanol and hexane under air-free conditions when the products are formed in the reactions of carbon-centered radicals. The probability of the reaction of the test compounds with alkyl radicals increases with a decrease in the BDE for the OH groups present in these compounds. The carbonyl group in compounds (IV-VIII) makes them efficient oxidants of α-hydroxyalkyl radicals, thus resulting in a change in the product composition for the ethanol radiolysis in presence of these compounds.