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Kinetics and mechanism of the oxidation of acetylacetone by permanganate ion
Author(s) -
Jáky Miklós,
Szammer János,
SimonTrompler Edit
Publication year - 2006
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20177
Subject(s) - chemistry , acetylacetone , permanganate , enol , kinetics , photochemistry , double bond , catalysis , reaction rate constant , nucleophile , delocalized electron , ion , inorganic chemistry , reaction mechanism , organic chemistry , physics , quantum mechanics
The kinetics and mechanism of permanganate ion oxidation of acetylacetone (Acac) was studied in acidic and alkaline media. The rate constants for keto, enol, and enolate anions were determined and discussed. Delocalization of the π‐electrons of the double bond by conjugation results in a slower oxidation rate of enol than can be usually observed for unsaturated compounds. In the case of the keto form, the acid‐catalyzed nucleophilic attack of permanganate ion occurs on the carbonyl‐C atom. For enolate anion a mechanism with basis‐catalyzed electron abstraction is suggested. © 2006 Wiley Periodicals, Inc. Int J Chem Kinet 38: 444–450, 2006