Abstract
Proton transfer reactions are advantageously investigated in low‐dielectric‐constant apolar aprotic solvents where specific solute–solvent interactions are greatly minimized, if not eliminated, and proton transfer occurs directly. An intriguing feature of these reactions is their general acid/base‐catalyzed kinetics with a timescale over microseconds to minutes. Proton‐coupled electron transfer (PCET), a great promise in the development of renewable energy sources, is an emerging application of the reactions. This article is an updated review of the post‐1980 developments in understanding the mechanism of proton transfer reactions, quantitative structure–reactivity relationships, acid/base‐catalyzed molecular rearrangements, reverse trends between acidity parameters and 13C δco (a measure of electron population at the carboxyl carbon) in aromatic carboxylic acids, coupling of proton transfer with electron transfer, and PCET reactions in suitably designed model systems in apolar aprotic solvents for renewable energy devices. Copyright © 2015 John Wiley & Sons, Ltd.
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