Abstract
The kinetics of oxidation of amines (EtNH2, Et2NH, Et3N) and aminoalcohols [H2NCH2CH2OH, H2N(CH2)3OH, (CH2CH2OH)2NH, (CH2CH2OH)3N] by N-bromosuccinimide (NBS) have been studied in aqueous HClO4 with PdCl2 as catalyst, and in the presence of Hg(OAc)2 to ensure oxidation by pure NBS. The order of reaction with respect to NBS was unity, however, an increase in [NBS]0 resulted in a decrease in the rate constant. The rate was directly proportional to [PdII] for the aminoalcohols while for EtNH2 the rate was proportional to k + k″[PdII] (where k and k″ are rate constants for the uncatalysed and catalysed paths, respectively). Retarding effects for HClO4, succinimide, Cl− and AcOH on the rate of oxidation were observed. The kinetic data support the formation of [PdII-A] and [PdII-(A)2] complexes (where A represents amine or aminoalcohol). A mechanism, consistent with the observed kinetic data, is proposed.
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