Paper chromatography and chemical structure

Abstract

A series of o-nitroso derivatives of phenols, alkoxyphenols, coumaranols and chromanols have been chromatographed. Two reversed phase and one direct phase system have been used. The correlation of the R_M values of these compounds with their structure is at present impossible, being complicated by the combined occurrence of tautomerism and internal hydrogen bonding. Since these factors are interdependent and since they also depend on the nature of the solvents, the chromatography of o-nitrosophenols cannot be satisfactorily interpreted in terms of the electronic structure of the parent phenols or the relevant bond orders in the parent hydrocarbons.