Español

Abstract

Salts of arenediazonium ions are very often used in organic synthesis with many purposes. Likewise, arenediazonium ions are frequently used in various industrial procedures. The relative ease to be obtained from their precursors present in the environment, foods, or drugs as well as the recognized mutagenic and/or carcinogenic capacity of the ions themselves or the other species derived from them in dediazoniation processes, justify the interest of arenediazonium ions from a health point of view. There are several aspects regarding arenediazonium ions chemistry and the mechanism of interaction with
biological macromolecules which remains partially unknown becoming subject of investigation nowadays. Among those aspects could be included, the ions reactivity as a function of the kind of chemical bond between diazonium group and the rest of the molecule, the identity of the genotoxic agent, the exact site where the genotoxic agent induces the DNA damage and whether that damage is produced as a result of a direct attack of the genotoxic agent or occurs in a secondary process. Finally, is also unknown if induced DNA damages by arenediazonium ions really cause carcinogenic effects subsequently. The dediazoniation reactions combine homolytic and heterolytic processes. The present review deals with the fundamental aspects of both mechanisms making special emphasis on the homolytic process originating the appearance of aryl radical which has been considered in many cases as ultimate genotoxic agent in the interaction between arenediazonium ions and DNA. In addition, a particular case of dediazoniation is considered in this review. The degrlUÚltion of the p-hydroxybenzenediazonium tetrafluorborate in a neutral aqueous medium is proposed that occurs by three pathways wherein aryl and hydroxyphenylperoxyl radicals appear in volved. Moreover, a possible side reaction forming hydroxyl radical is suggested.