T-for-H exchange reaction between HTO vapor and two functional groups in an aromatic compound in a gas-solid system

Abstract

The hydrogen-isotope exchange reaction (T-for-H exchange reaction) between HTO vapor and an aromatic compound having two different kinds of functional groups has been observed at several temperatures. The rate constant (k) for each functional group in the T-for-H exchange reaction was obtained by using both theA″-McKay plot method and the data observed. Comparing thesek with each other has led to the following four conclusions in the T-for-H exchange reaction. (1) The reactivity of both the COOH and OH groups increases with a rise in temperature. (2) As to the degree of the effect of the COOH group on the reactivity of monosubstituted phenols, the degree inp-hydroxybenzoic acid is greater than that inm-hydroxybenzoic acid. (3) The HAMMETT rule is useful for estimating the reactivity of a certain aromatic compound. (4) TheA″-McKay plot method is also useful not only investigating the reactivity of the compounds having one kind of functional group, but also doing the reactivity of the compounds having two different kinds of functional groups.