Intramolecular general base and intermolecular nucleophilic catalysis of carbonate ester hydrolysis. Hydrolysis of ethyl 2-hydroxy-5-nitrophenyl carbonate

1972 ◽  
Vol 94 (8) ◽  
pp. 2837-2842 ◽  
Author(s):  
Thomas H. Fife ◽  
J. E. C. Hutchins
Keyword(s):  
Ester Hydrolysis ◽  
Nucleophilic Catalysis ◽  
General Base ◽  
Hydrolysis Of

ChemInform Abstract: INTRAMOLECULAR GENERAL BASE CATALYSIS OF INTRAMOLECULAR NUCLEOPHILIC CATALYSIS OF ESTER HYDROLYSIS

1974 ◽  
Vol 5 (33) ◽  
pp. no-no
Author(s):  
ANTHONY J. KIRBY ◽  
GORDON J. LLOYD
Keyword(s):  
Ester Hydrolysis ◽  
Base Catalysis ◽  
Nucleophilic Catalysis ◽  
General Base

Nucleophilic Catalysis by HPO42- in the Hydrolysis of Cr2O72-. Formation and Decay of HO3POCrO32-

1994 ◽  
Vol 47 (12) ◽  
pp. 2283
Author(s):  
NE Brasch ◽  
DA Buckingham ◽  
CR Clark
Keyword(s):  
Coordination Number ◽  
Phosphate Buffer ◽  
Initial Reaction ◽  
Nucleophilic Catalysis ◽  
Stepwise Mechanism ◽  
General Base ◽  
Chromium Vi ◽  
Rapid Formation ◽  
Hydrolysis Of ◽  
Spontaneous Reaction

The initial reaction of Cr2O72- in phosphate buffer (pH 6.03-8.54, 25.0°C, I = 1.0 M NaClO4) follows the rate law kobs = kK [HPO42]/(1+K[HPO42-]). This is interpreted as arising from the reversible and rapid formation of a chromium(VI)- phosphato intermediate of increased coordination number (K = 5.5�1.3M-1), and rate-determining loss of CrO42- from this species (k = 4.4�0.5 s-1) to give HO3POCrO32- ( pKc a= 6.96). This appears to be the first clear demonstration of an addition-elimination (stepwise) mechanism for substitution at chromium (VI). Subsequent equilibration of HO3POCrO32- to give HCrO4- and H2PO4- (K = 5.95�1.90 M-1) is seen as a separate process which is subject to specific H+ and OH-, and general base (HPO42-) catalysis, in addition to a spontaneous reaction.

Intramolecular General Base Catalyzed Ester Hydrolysis. The Hydrolysis of 2-Aminobenzoate Esters

2002 ◽  
Vol 67 (10) ◽  
pp. 3179-3183 ◽  
Author(s):  
Thomas H. Fife ◽  
Randhir Singh ◽  
Ramesh Bembi
Keyword(s):  
Ester Hydrolysis ◽  
General Base ◽  
Hydrolysis Of

Hydrolysis of aspirin. Intramolecular general base catalysis of ester hydrolysis

1967 ◽  
Vol 89 (19) ◽  
pp. 4857-4863 ◽  
Author(s):  
A. R. Fersht ◽  
Anthony J. Kirby
Keyword(s):  
Ester Hydrolysis ◽  
Base Catalysis ◽  
General Base ◽  
Hydrolysis Of
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