Nitration and hydroxylation of substituted phenols by peroxynitrite. Kinetic feature and an alternative mechanistic view

Article abstract of DOI:10.1016/S0040-4039(99)01238-1

The reaction of peroxynitrite (ONOO^-) with a series of para-substituted phenols has been examined in aqueous phosphate buffer and acetonitrile solutions. Major products were the corresponding 2-nitro derivative and the 4-substituted catechol. Kinetic study showed good correlation with Hammett σ(p)⁺ parameters and reduction potentials, suggesting the possible one-electron transfer process involving the nitrosoniun ion (NO⁺) as initial electrophile generated from peroxynitrous acid.