855403-42-8Relevant articles and documents
A quantitative structure-reactivity assessment of phenols by investigation of rapid iodination kinetics using hydrodynamic voltammetry: Applicability of the Hammett equation in aqueous medium
Borkar, Vitthal T.,Bonde, Shantaram L.,Dangat, Vijay T.
, p. 693 - 702 (2013/10/21)
Halogenations of aromatic substrates in aqueous medium are essentially electrophilic substitutions proceeding at rates concomitant with the nature of the substrates and substituent motifs. Kinetics as an investigatory tool for the quantitative assessment of the structure-reactivity correlation in these reactions for a diverse range of substrates has rarely been reported, presumably due to the rapidity of these reactions in aqueous medium. We have used hydrodynamic voltammetry to investigate the rapid kinetics of uncatalyzed iodination of phenol and eight substituted phenols by iodine monochloride at constant pH in aqueous medium. The Arrhenius plots for these reactions yield comprehensive kinetic and thermodynamic data. The quantitative structure-reactivity correlation stemming from the regio- and stereospecificity of the substituent motifs on the substrates has been examined through the Hammett plot, which shows a negative slope of 1.87. The magnitudes of the rate constants, energies of activation, frequency factors, and entropy change obtained for the nine fast reactions reported, reflect the relative ease of the reaction dynamics in quantitative terms thereby ascertaining the relative reactivities of the phenols studied herein.
Kinetics and Mechanism of Iodination of Phenol and Substituted Phenols by Iodine Monochloride in Aqueous Acetic Acid
Prasada Rao, M. D.,Padmanabha, J.
, p. 133 - 135 (2007/10/02)
In the title reactions the order with respect to ICl is unity and with respect to the substrate it is fractional in the concentration range studied.The effect of varying is negligible at lower acid (HClO) concentrations but at higher (> 0.01 M) there is unit dependence on .From the double reciprocal plot of 1/k1 versus 1/ the decomposition constants have been evaluated.Using these a linear ρ+ - ?+ plot is obtained indicating C-iodination.A mechanism consistent with the results obtained has been postulated.