The hydrogen atom transfer reactivity of sulfinic acids.

ABSTRACT: Sulfinic acids (RSO₂H) have a reputation for being difficult reagents due to their facile autoxidation. Nevertheless, they have recently been employed as key reagents in a variety of useful radical chain reactions. To account for this paradox and enable further development of radical reactions employing sulfinic acids, we have characterized the thermodynamics and kinetics of their H-atom transfer reactions for the first time. The O-H bond dissociation enthalpy (BDE) of sulfinic acids was determined by radical equilibration to be ∼78 kcal mol^-1; roughly halfway between the RS-H BDE in thiols (∼87 kcal mol^-1) and RSO-H BDE in sulfenic acids (∼70 kcal mol^-1). Regardless, RSH, RSOH and RSO₂H have relatively similar inherent H-atom transfer

SUBMITTER: Griesser M 

PROVIDER: S-EPMC6148200 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature