Correlation of Nucleophilic Reactivity, Dissociation Constant and Proton Magnetic Resonance of Some 2‐Substituted Naphthols

Abstract

The rates of reaction of a series of substituted naphthoxides with 1‐chloro‐2,4‐dinitrobenzene in methanol, and the pKa values of the naphthols in 50% methanol have been measured. A linear free energy relationship applies well to these reactions. The rate constants are correlated with the pKa values of the corresponding naphthols via the Brönsted equation giving a β values of 0.94. A linear correlation between ΔH‡ and ΔS‡ is indicative of single mechanism. The nmr spectra of the substituted naphthols have been measured in DMSO·d6.