The Effects of Substituents on the pKα, Values of "meta"-Substituted 1- and 2-Naphthols

Abstract

p K a values (H2O at 25°C) have been measured for 3-substituted 1-naphthols and 4-substituted 2-naphthols and the results show that the behaviour of these compounds is similar to that of the equivalent naphthylamines. ?p K a values satisfy equations of the type: ?p K a = ?IsI + ?RsR, where sI and sR are inductive and mesomeric constants applying to meta-substituents. Reaction constants ?I and ?M are interpreted in terms of the energy terms involved and can be correlated with the a-electron distributions in the molecular species concerned.