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Protolytic properties of 2-acylthioacetamides

Concentration acidity of 2-acylthioacetamides dissolved in DMSO-H2O was measured by the method of pH-metric titration. The data obtained were extrapolated for the determination of pK a values of 2-acylthioacetamides in water and DMSO. We found that in aqueous solutions the acidity of thioacetarylamide (pK a = 5.75–6.01) was almost independent of the nature of substituents in their N-phenyl rings, whereas in DMSO solution the nature of substituents significantly affects their ionization constants (pK a = 7.88–11.70). The graphs were displayed and the acidity of N-aryl-3-oxobutanethioamides dependence on the Hammett constants of meta- and para-substituents in the phenyl rings derived. Water is shown to be a leveling, and DMSO a differentiating solvent for 2-acylthioacetamides.

Authors:   V. N. Britsun, V. A. Doroshchuk, V. S. Starova, A. B. Ryabitskii, M. O. Lozinskii
Journal:   Russian Journal of General Chemistry
Volume:   82
edition:   10
Year:   2012
Pages:   1700
DOI:   10.1134/S1070363212100106
Publication date:   19-Nov-2012
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