A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pK_a 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 pK_a 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 pK_a values determined herein with the nucleophilicity of the corresponding carbenes.

中文翻译：

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阳离子结构对三唑鎓盐在二甲亚砜中酸度的影响。

制备了一系列因其不同的电子和空间特性而选择的三唑鎓盐，并使用包围指示剂方法在DMSO中于25°C下测定了其p K _a值。各系统的结构变化在所述三唑阳离子的酸性的效果已被认为，特别是检查系统改变电子性质，通过使用量化哈米特的效果σ参数。还报道了产生中性卡宾的偶氮盐的第一个p K _a值。这些新数据允许选择适当的碱基，以使这种三唑鎓盐去质子化，并具有使p K _a相关的潜力。 本文通过相应的羧苯甲酸酯的亲核性确定的值。