Primary amine diazeniumdiolate ions of structure {RNN(O)NOR′}− as ambident nucleophiles

An O2-substituted primary amine diazeniumdiolate RHN–N(O)NOR′ is ionized to an anion that attacks an electrophile R″X via either of two nitrogens to form both RR″N–N(O)NOR′ and R–NN(O)–N(R″)OR′. The bidentate character of such anions should be kept in mind when planning or evaluating drug discovery efforts involving diazeniumdiolates of structure RHN–N(O)NOR′.