The Journal of Organic Chemistry

The pKa of areneselenenic acids

SI Kang, JL Kice

Index: Kang, Sang-Ihn; Kice, John L. Journal of Organic Chemistry, 1986 , vol. 51, # 3 p. 287 - 290

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Citation Number: 7

Abstract

The pK,'s of o-nitrobenzeneselenenic acid (la) and three 4-substituted-2- nitrobenzeneselenenic acids (lb-d) have been determined at 25" C in water. A Hammett plot of the pK,'s gives ap value for the ionization of ArSeOH (eq 3) of+ 1.4. The pK, of la is 10.45, which makes it 2.8 times weaker as an acid than phenol. Areneselenenic acids are therefore surprisingly weak acids. If the only influence of the o-nitro group on the acidity of la is its ...