N.M.R. spectra of 'p-nitrosophenol' and its methyl derivatives

Abstract

On the basis of N.M.R. spectra, supported by u.v. and i.r. data, it can be concluded that "p-nitrosophenol" and several of its methyl derivatives exist predominantly in the benzoquinone monoxime form in organic solvents and that in aqueous solutions the corresponding potassium salts have the negative charge largely on the oxime oxygen. The protons on the α-carbon syn to the quinone monoxime hydroxyl are deshielded with respect to the anti protons but this relationship appears to be reversed in the anions. The N.M.R. spectra of some p-nitrosoanisoles and quinone monoxime methyl ethers are given and syn-anti equilibria and long-range spin-spin coupling are discussed.