EFFECT OF INTRAMOLECULAR HYDROGEN BONDING ON IONIZATION CONSTANTS OF SUBSTITUTED SALICYLIC ACIDS

Abstract

Ionization constants at 25 °C have been determined by a spectrophotometric method for 17 substituted salicylic acids. These have been fitted to the simple Hammett relationship and to the extended one proposed by Jaffe, which takes into account the transmission of substituent effects by the o-hydroxy group. The results with Jaffe's equation show that substituent effects on acidity are transmitted only slightly, if at all, through the intramolecular hydrogen bond of a chelate ring. Possible interpretations of the results are discussed.