Kinetics and Mechanism of Bromine Addition to Derivatives of Unsaturated Aliphatic Carboxylic Acids in Aqueous Solution

Article abstract of DOI:10.1246/bcsj.57.1394

This paper deals with the kinetics of bromine addition to unsaturated compounds in presence of added bromide ions at 22, 30, 38, 46, and 54 deg C.The substrates used were acrylamide (AAm), methyl acrylate (MA), ethyl acrylate (EA), butyl acrylate (BA), t-butyl acrylate (tBA), methacrylamide (MAAm), methyl methacrylate (MMA), ethyl methacrylate (EMA), methyl crotonate (MC), and ethyl crotonate (EC).The kinetics was followed potentiometrically.The activation parameters (ΔH^*, ΔS^*, and ΔG^*) were calculated and compared.Estimation of product ratio of bromohydrin to dibromide showed the absence of any correlation of the product formation with reactivity of the substrates.The observed parameters are discussed in relation to the proposed reaction mechanisms.