COMPARISON OF AROMATIC AND ALIPHATIC DICARBOXYLIC-ACID IN REACTIVITY USING HYDROGEN-ISOTOPE EXCHANGE-REACTION IN A GAS-SOLID SYSTEM

The hydrogen-isotope exchange reaction between aromatic (alicyclic, or normal chain aliphatic) dicarboxylic acid (solid) and HTO vapor was observed at 40 degrees C similar to 80 degrees C to reveal the reactivity of the material having the same two functional groups. The A''-McKay plot method was used to determine its rate constant. From the rate constants thus determined, the following three findings have been clarified in the reaction. (1) The reactivity of aromatic dicarboxylic acid is similar to that of normal chain aliphatic dicarboxylic acid, and is greater than that of alicyclic acid. (2) Concerning 1,2- or 1,4-cyclohexanedicarboxylic acid, cis-isomer is similar to trans-isomer in reactivity. (3) The reactivity of isophthalic acid is larger than that of benzoic acid, and seems to follow the Hammett rule.