Forty-four substituted 2-naphthoic acids, two substituted 1-naphthoic acids and some of their corresponding methyl esters have been synthesized. The substituents are the nitro, cyano, fluoro, chloro, bromo, iodo, methyl, hydroxyl, methoxy, amino and dimethylamino groups. The apparent pKa - values of these acids and the unsubstituted maphthoic acids have been determined for 50% v/v aqueous ethanol at 25o C. The rates of alkaline hydrolysis in 70% v/v aqueous dioxan at 25o were determined for the methyl esters of seven 6 - substituted-2 – naphthoic acids and five 7 - substituted - 2 - naphthoic acids.
This data has permitted a test of the Hammett relationship for the naphthalene system. Dewar and Grisdale's simple general expression for aromatic substituent effects was examined further using the apparent dissociation data. The latter section of the thesis has been devoted to discussing specific substituent influences in individual dispositions.
The nomenclature used in the discussion for indicating substituent - reaction site disposition in the naphthalene system is shown by Fig. 7, Chapter 5. The alternative, 1 and 2 for œ and ß respectively (reaction site), was adopted in Chapter 2 (Syntheses).