Collect. Czech. Chem. Commun. 1994, 59, 391-400

Effects of Substituents and Medium on Acidity of α,α-Bis(butylsulfonyl)toluenes

Miroslav Ludwig, Jan Petržílek, Jiří Kulhánek and Oldřich Pytela

Department of Organic Chemistry, University of Chemical Technology, 532 10 Pardubice, Czech Republic


Seven substituted α,α-bis(butylsulfonyl)toluenes and three 2-aryl-1,1,3,3-tetraoxo-1,3-dithiolanes have been prepared and their 1H NMR, IR, and MS spectra measured. The pKHA values of the substituted α,α-bis(butylsulfonyl)toluenes have been determined by potentiometric titration in dimethyl sulfoxide, dimethylformamide, and 80% (v/v) mixture of dimethyl sulfoxide and water. The results are interpreted by the Yukawa-Tsuno relationship (parameter r = 0.43 - 0.49) and classified in relation to analogous N- and O-acids by the methods with latent variables (the method of conjugated deviations).