An Acidity Scale of Triazolium-Based NHC Precursors in DMSO

Abstract

An acidity scale of triazolium-based N-heterocyclic carbene precursors was established by measuring 25 compounds’ (<b>10a</b>–<b>15b</b>) equilibrium acidities in dimethyl sulfoxide (DMSO) solution using overlapping indicator method. The p<i>K</i><sub>a</sub> values ranged from 12.08 to 15.5, responding not only to the <i>N</i>-aryl motif, but also to the core structure. Excellent correlation was observed between the p<i>K</i><sub>a</sub> values and the Hammett substituent constants (σ<sub>p</sub>)

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