Impact of substitution on reactions and stability of one-electron oxidised phenyl sulfonates in aqueous solution.

ABSTRACT: Highly reactive aromatic cation radicals have been invoked lately in synthetic routes and in the degradation pathways of hydrocarbon-based polymers. Changes in the electron density of aromatic compounds are expected to alter the reaction pathway following one electron oxidation through altering the pK_a of the formed intermediate cation radical. Electron-donating groups increase its stability, however, little experimental data are known. While, in theory, the cation radical can be repaired by simple electron transfer, electron transfer to or from its deprotonated form, the hydroxycyclohexadienyl radical, will cause permanent modification or degradation. Time-resolved absorption spectroscopy indicates a pK_a ≈ 2-3 for the 4-(tert-butyl)-2-methoxyphen

SUBMITTER: Nemeth T 

PROVIDER: S-EPMC8725611 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature