Diazeniumdiolates (DAZDs) are effective NO delivery agents, releasing nitric oxide upon stimulation by light, heat, or protons. We recently synthesized the triphenylmethyl (trityl) C-DAZD, [K(18-crown-6)][O2N2CPh3] (1) in excellent yields. Photolysis of 1 generated NO and Ph3CH as the major products. In contrast, reaction of 1 with AgPF6 resulted in the formation of O(CPh3)2 and N2O as the major products. Importantly, the release of NO vs N2O by 1 represents a rare instance of stimulus-dependent product formation. The salt metathesis chemistry of 1, and the NO-release chemistry of the resulting complexes, will also be discussed.

Synthesis of a trityl C-diazeniumdiolate and an exploration of its NO-releasing properties

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ACS Fall 2022

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