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

Methyltriazenes are believed to be the active metabolite of triazene containing anti-neoplastic agents, such as Dacarbazine and Temozolomide. It has been proposed that these agents methylate the O6-oxygen of guanine. Methylguanine formation is believed to be responsible for their observed cytotoxic properties. To facilitate a better understanding of this proposed mechanism, a series of ab initio calculations of the bimolecular nucleophilic substitution (SN2) reaction between 1- and 3-methyltriazene and the halide ions were undertaken, the results of which are presented here.