Observing Aqueous Proton-Uptake Reactions Triggered by Light

[Image: see text] Proton-transfer reactions in water are essential to chemistry and biology. Earlier studies reported on aqueous proton-transfer mechanisms by observing light-triggered reactions of strong (photo)acids and weak bases. Similar studies on strong (photo)base–weak acid reactions would also be of interest because earlier theoretical works found evidence for mechanistic differences between aqueous H(+) and OH(–) transfer. In this work, we study the reaction of actinoquinol, a water-soluble strong photobase, with the water solvent and the weak acid succinimide. We find that in aqueous solutions containing succinimide, the proton-transfer reaction proceeds via two parallel and competing reaction channels. In the first channel, actinoquinol extracts a proton from water, after which the newly generated hydroxide ion is scavenged by succinimide. In the second channel, succinimide forms a hydrogen-bonded complex with actinoquinol and the proton is transferred directly. Interestingly, we do not observe proton conduction in water-separated actinoquinol–succinimide complexes, which makes the newly studied strong base–weak acid reaction essentially different from previously studied strong acid–weak base reactions.