o-iodoxybenzoic acid (IBX): pKa and proton-affinity analysis

Abstract

(Chemical Equation Presented) Not just a pretty oxidant! IBX (1-Hydroxy-1,2-benziodoxol-3(1H)-on-1-oxide), an important oxidant in organic synthesis, is shown to be relatively acidic on the organic scale. The pK a value and proton affinity of IBX were determined both in silico and in vitro. This acidity could explain the non-oxidation processes mediated by IBX. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.