ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The behaviour of dimethylaminoethylbenzoate N-oxide and similar esters during alkaline and neutral hydrolysis is investigated, using comparative rate studies and 18O tracer techniques. Whereas in an alkaline medium the amine oxide ester is somewhat less reactive than benzoylcholine, neutral hydrolysis is faster by a factor of about 102. It was found, furthermore, that neutral hydrolysis of benzoylcholine is appreciably accelerated (ca. 50-fold) if dimethylaminoethanol N-oxide is added in equimolar amount, the amine oxide alcohol thus representing a cholinesterase model. On the basis of 18O tracer experiments presented here, and of indications taken from the literature, an attempt is made to interpret the results in terms of mechanisms involving, respectively, intramolecular and intermolecular bifunctional catalysis.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19590420535
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