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Der Mechanismus der Hydrolyse von Chlortriazinen in protischen Lösungsmitteln . II. Mitteilung Über nukleophile uromatische Substitutionen
Author(s) -
Rys P.,
Schmitz A.,
Zollinger H.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540115
Subject(s) - chemistry , deprotonation , medicinal chemistry , hydrolysis , protonation , acetone , chloride , kinetics , triazine , ion , organic chemistry , physics , quantum mechanics
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.