Der Mechanismus der Hydrolyse von Chlortriazinen in protischen Lösungsmitteln. II. Mitteilung Über nukleophile uromatische Substitutionen

The complex kinetics found for the hydrolysis of 1, 3, 5‐trichloro‐s‐triazine in 9/91% (v) acetone/water at 10.0°C have been evaluated as a function of the hydroxyl ion and the acetate ion concentration using an analogue computer. The kinetics are consistent with a nonsteady state mechanism in which the primary intermediate anion is protonated giving a neutral species whose concentration goes through a maximum during the course of the reaction. This secondary intermediate forms the final product by deprotonation and release of a chloride ion. The product itself can undergo a second (reversible) deprotonation. In dimethylsulfoxide the analogous intermediate of the hydrolysis of 1, 3‐dimethoxy‐5‐chloro‐s‐triazine can be identified by analysis of the NMR. and UV. spectra.