MEASUREMENT OF THE DONOR STRENGTH OF SUBS TITUTED 1-NAPHTHOLS

The oxidation potential of various substituted naphthols is available by cyclovoltammetry. The donor strength of substituents on the oxidati on potential may be explained on the base of substituent increments. W hen correlating the oxidation potential with the transition energy of charge transfer complexes with TCNE, 1-naphthols with 8-alkoxy substit uents and naphthols without oxygen in position 8 are giving different correlation curves. The experimental values correlate well with semiem pirically calculated HOMO energies. Our measurements allow to predict the oxidation potentials of hitherto unknown substituted 1-naphthols w ith high probality. Thus, it may be possible to synthesize 1-naphthols with a defined oxidation potential.