Issue 1, 2020

The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide

Abstract

A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each systematic structural variation upon the acidity of the triazolium cation has been considered, in particular examining the effects of systematically altering electronic properties, quantified through the use of Hammett σ parameters. The first pKa value for an azolium salt that generates a mesionic carbene is also reported. These new data allow for the selection of appropriate bases for the deprotonation of such triazolium salts and the potential to correlate the pKa values determined herein with the nucleophilicity of the corresponding carbenes.

Graphical abstract: The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide

Supplementary files

Article information

Article type
Paper
Submitted
18 Oct 2019
Accepted
14 Nov 2019
First published
14 Nov 2019

Org. Biomol. Chem., 2020,18, 66-75

The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide

N. Konstandaras, M. H. Dunn, M. S. Guerry, C. D. Barnett, M. L. Cole and J. B. Harper, Org. Biomol. Chem., 2020, 18, 66 DOI: 10.1039/C9OB02258A

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