The effect of 4-substitution on some properties of the O–H bond in 1-naphthols

The effects of 4-substitution on some of those properties of the O–H bond in 1-naphthols which reflect its hydrogen bonding tendency have been studied. The properties investigated were the near infrared O–H stretching frequencies in cyclohexane and dioxan solutions, the association constant of complex formation with dioxan and the affinity of adsorption at an activated alumina/solution interface. A series of 4-substituted-1-naphthols has been prepared and comparisons in behaviour with 4-substituted phenols have been made throughout. [Continues.]