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Phenylsulfinic acid : ウィキペディア英語版
Phenylsulfinic acid

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Phenylsulfinic acid is an organosulfur compound with the formula C6H5SO2H. It is a colorless or white crystalline solid that is usually stored in the form of its sodium salt. In aqueous solution it is strongly acidic and is easily oxidized in air. Phenylsulfinic acid and its esters are chiral.
==Acidity==
Although many sources report the pKa value as somewhere around 1.30,〔a) A. T. Fuller, I. M. Tonkin and J. Walker, J. Chem. Soc., 1945, 636; b) S. Smiles and C. M. Bere, "Organic Syntheses," Coll. Vol. I, ed. by A. H. Blatt, John Wiley and Sons, Inc., New York, 1948, p. 7; c) E. Bader and H. D. Hermann, Chem. Ber., 88, 46 (1955); d) M. Kulka, Can. J. Chem., 32, 601 (1954).〕 these results are inconsistent. However, a reproducible method was developed by Filippo et al. in which the pKa was determined to be 2.764. This is a strong acid compared to its corresponding carboxylic acid, benzoic acid (pKa = 4.2), but weak when compared to its corresponding sulfonic acid (pKa = -6.5).〔E. P. Serjeant, B. Dempsey. "Ionization Constants of Organic Acids in Solution" IUPAC Data, Series No. 23 (Pergamon Press, Oxford)〕

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