Hydroxyl Group (V)1and Imidazole (X)2Catalysis. The General Base Catalysis of Ester Hydrolysis by Imidazole and the Influence of a Neighboring Hydroxyl Group

1962 ◽  
Vol 84 (15) ◽  
pp. 3012-3018 ◽  
Author(s):  
Thomas C. Bruice ◽  
Thomas H. Fife ◽  
John J. Bruno ◽  
Patricia. Benkovic
Keyword(s):  
Ester Hydrolysis ◽  
Base Catalysis ◽  
Hydroxyl Group ◽  
Group V ◽  
General Base

Kinetics and mechanism of the bromination of phenols in aqueous solution. Evidence of general base catalysis of bromine attack

1990 ◽  
Vol 68 (10) ◽  
pp. 1769-1773 ◽  
Author(s):  
Oswald S. Tee ◽  
N. Rani Iyengar
Keyword(s):  
Aqueous Solution ◽  
Kinetics And Mechanism ◽  
Base Catalysis ◽  
Hydroxyl Group ◽  
Molecular Bromine ◽  
Electrophilic Attack ◽  
General Base ◽  
Carboxylate Anions

The reactions of bromine with phenol, 4-bromophenol, and 4-methylphenol (p-cresol) in aqueous solution are catalyzed by carboxylate anions, confirming the suggestions of earlier work. The results are consistent with deprotonation of the phenol hydroxyl group by a general base occurring at more or less the same time as electrophilic attack by molecular bromine. Possible origins of the general base catalysis are discussed. Combined with earlier results, the present findings suggest that a protonated cyclohexadienone is not a mandatory intermediate in phenol bromination; it can be avoided in both the formation of and enolization of the cyclohexadienone intermediate by general catalysis. Keywords: bromination, phenol, mechanism, catalysis, kinetics.

ChemInform Abstract: General Base Catalysis of Ester Hydrolysis.

ChemInform ◽  
2010 ◽  
Vol 24 (46) ◽  
pp. no-no
Author(s):  
D. STEFANIDIS ◽  
W. P. JENCKS
Keyword(s):  
Ester Hydrolysis ◽  
Base Catalysis ◽  
General Base

General base catalysis of ester hydrolysis

1993 ◽  
Vol 115 (14) ◽  
pp. 6045-6050 ◽  
Author(s):  
Dimitrios Stefanidis ◽  
William P. Jencks
Keyword(s):  
Ester Hydrolysis ◽  
Base Catalysis ◽  
General Base
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