Cephalexin degradation initiated by OH radicals: theoretical prediction of the mechanisms and the toxicity of byproducts

In this work, the density functional theory is used to study the local reactivity of cephalexin (CLX) to radical attack and explain the mechanism of the reaction between CLX and hydroxyl radical attack leading to degradation byproducts. The reaction between •OH and CLX is supposed to lead to either an addition of a hydroxyl radical or an abstraction of a hydrogen. The results showed that the affinity of cephalexin for addition reactions increases as it passes from the gas to the aqueous phase and decreases as it passes from the neutral to the ionized form. Thermodynamic data confirmed that OH addition radicals ( R add ) are thermodynamically favored over H abstraction radicals ( R abs ). The ecotoxicity assessments of CLX and its byproducts are estimated from the acute toxicities toward green algae, Daphnia , and fish. The formation of byproducts is safe for aquatic organisms, and only one byproduct is harmful to Daphnia . Graphical abstract