Synthesis and Electronic Properties of the 1-Naphthoxyl Radical

Naphthoxyl radicals can be stabilized by the appropriate introduction of sterically hindered groups at the 2- and 4-positions. In this study, a new 1-naphthoxyl derivative was synthesized, and its spin density distribution and redox potential were determined. The time course of its ESR spectrum revealed that the half-life of such a radical in a degassed sealed state was 4.0 days. As a result of this study, valuable information has become available concerning the electronic structure and stabilization strategy of the naphthoxyl radicals. The 1-naphthoxyl radical, which possess a structure located between the phenoxyl and anthroxyl species in the aryloxyl radical series, was moderately stabilized by introducing sterically hindered protecting groups at the 2- and 4-positions. The spin density distribution of the synthesized radical was confirmed by ESR spectroscopy, and its half-life was determined to be 4.0 days.