Heavy-atom isotope effects on the acid-catalyzed hydrolysis of methyl benzoate
Results of the use of a previously reported technique of four-heavy atom isotope effects for study of the acid-catalyzed hydrolysis of methyl benzoate are reported. Ether oxygen and methyl carbon isotope effects on the reaction were measured by the usual natural-abundance isotope-ratio technique. The carbonyl oxygen isotope effect was measured by the pseudo-natural-abundance double-label method as was the carbonyl carbon isotope effect. The results led to the assumption that the hydrolysis of methyl benzoate proceeds by way of a tetrahedral intermediate. The small amount of oxygen exchange with the solvent that accompanies the hydrolysis indicated that it is intermediate formation rather than decomposition that is rate determining. The small magnitude of the observed carbon isotope effect on the acid-catalyzed hydrolysis of methyl benzoate compared to carbon isotope effects on other reactions of this compound indicate that the transition state is relatively reactant-like. (BLM)
- Research Organization:
- Univ. of Wisconsin, Madison
- OSTI ID:
- 6202422
- Journal Information:
- J. Org. Chem.; (United States), Vol. 46:10
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
BENZOIC ACID
HYDROLYSIS
CARBON 13
ISOTOPE EFFECTS
OXYGEN 18
CATALYSIS
CATALYTIC EFFECTS
EXPERIMENTAL DATA
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
DECOMPOSITION
EVEN-EVEN NUCLEI
EVEN-ODD NUCLEI
INFORMATION
ISOTOPES
LIGHT NUCLEI
LYSIS
MONOCARBOXYLIC ACIDS
NUCLEI
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXYGEN ISOTOPES
SOLVOLYSIS
STABLE ISOTOPES
400302* - Organic Chemistry- Isotope Effects- (-1987)