When resorcinol is chlorinated with hypochlorous acid (HOCl) in a 1:1 molar ratio, the product mixture contains an unexpectedly high concentration of dichloro- and tricholororesorcinol. A possible hypothesis is that when the intermediate formed during the first chlorination, shown below, is produced, that it reacts faster with HOCl than it does with water to rearomatize. Since water is the solvent, and present in vast excess, for this hypothesis to be valid, the activation energy for the reaction of the intermediate with HOCl must be significantly lower than the activation energy of the reactive intermediate with water. The activation energies of the relevant reactions have been calculated at the density functional level. The results of these calculations and the insight that they bring to the reaction are the subject of this presentation.

Computational modeling of the kinetics of the reaction of hypochlorous acid with resorcinol

251st National Meeting (2016)

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