Collect. Czech. Chem. Commun. 1997, 62, 1737-1746

Acid-Base Properties of Substituted Naphthoic Acids in Nonaqueous Media

Patrik Pařík and Miroslav Ludwig

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


Thirteen substituted 1-naphthoic acids have been prepared and their dissociation constants, along with those of twenty-five substituted 2-naphthoic acids, have been measured potentiometrically in methanol, N,N-dimethylformamide, pyridine, and acetonitrile. The pKHA values obtained have been treated by linear regression using four sets of substituent constants. The experimental data have also been interpreted by statistical methods using latent variables. The first latent variable calculated by these methods can be used as a new set of substituent constants for describing substituent effects in naphthalene skeleton.

Keywords: Naphthoic acids; Dissociation; Substituent effects; Solvent effect; Chemometrics.