Collect. Czech. Chem. Commun. 2000, 65, 385-394

Dissociation of Naphthoic Acids in Non-Aqueous Media. Comparison of Benzene and Naphthalene Skeletons

Patrik Paříka,*, Jitka Wolfováb and Miroslav Ludwiga

a Department of Organic Chemistry, University of Pardubice, nám. Čs. legií 565, 532 10 Pardubice, Czech Republic
b Department of Organic Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic


Seven monosubstituted 1-naphthoic acids were synthesized by new or modified procedures, and their dissociation constants were measured potentiometrically at 25 °C in methanol, acetonitrile, dimethylformamide, and pyridine. Dissociation constants of these along with thirteen substituted 1-naphthoic acids and twenty-five substituted 2-naphthoic acids previously studied were measured at 25 °C in ethanol and dimethyl sulfoxide. The pKHA values of 3- and 4-substituted 1-naphthoic acids were treated by simple linear regression and principal component analysis, and the results were used for comparison of model compounds and of corresponding 3- and 4-substituted benzoic acids with the aim of comparison of benzene and naphthalene skeletons. It has been found, the 3 and 4 positions of the 1-naphthyl system can roughly be compared with the meta and para positions of benzene, respectively.

Keywords: Naphthoic acids; Benzoic acids; Dissociation; Ionization constants; Substituent effects; Solvent effects; Chemometrics.

References: 42 live references.