Collect. Czech. Chem. Commun. 1998, 63, 85-93

Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures

Petr Mitaš, Miloš Sedlák and Jaromír Kaválek

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


The dissociation constants of substituted 2-(4-nitrobenzoylamino)alkanamides, N-[2-(4-nitrobenzoylamino)alkanoyl]pyrrolidines, and N-alkyl-4-nitrobenzamides have been measured spectrophotometrically in 60 and 80% v/v DMSO. The pKA values of these N-acids are discussed from the point of view of substituents at the acetamide α-carbon atom.

Keywords: Dissociation constants; Substituent effects; 2-(4-Nitrobenzoylamino)alkanamides; Solvent effects; Steric effects.