An ab initio study of the SN2 reaction of 1,3- and 3,3-dimethyltriazene with halide ions

It has been proposed that methyltriazenes methylate the O6-oxygen of guanine, resulting in the formation of methylguanine which is thought to be responsible for the cytotoxic properties of triazene-containing anti-neoplastic agents, such as Dacarbazine. The results of a series of model ab initio calculations of the bimolecular nucleophilic substitution (SN2) reaction between 1,3- and 3,3-dimethyltriazene and the halide ions are presented here. This second paper of a series of investigations of carbon centered SN2 reactions involving methyltriazenes and halide ions furthers our understanding of the proposed mechanism of triazene-containing anti-neoplastic agents.