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Theoretical studies on the acid hydrolysis of methyl carbamate

✍ Scribed by Ikchoon Lee; Chang Kon Kim; Byung Choon Lee

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
499 KB
Volume
8
Category
Article
ISSN
0192-8651

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✦ Synopsis

The mechanism of the A2 acid hydrolysis of methyl carbamate was investigated using MNDO method. The reaction was found to proceed in two steps: (1) the rate-determining nucleophilic attack of water on the carbonyl carbon of the N-protonated tautomer involving the tetrahedral TS; and (2) the fast subsequent proton abstraction by the leaving group, NH3, to form products. The mechanism is similar to that involved in the A2 hydrolysis of acetamide. Effects of substituents, R', R2, and R3 in R'OCONR2R3, on rates can be predicted by the changes in electron densities on alkoxy oxygen and N, in complete agreement with the experimental results. We concluded that there is no need for invoking two different mechanisms for amides and carbarnates since a common mechanism can easily accommodate all the experimental results.

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