Abstract
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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
