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Theoretical studies on the alkaline hydrolysis of N-Methylcarbamates

✍ Scribed by Toshiyuki Katagi

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
542 KB
Volume
11
Category
Article
ISSN
0192-8651

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✦ Synopsis

The reaction mechanisms of the alkaline hydrolysis of N-methylcarbamates were studied using the AM1 method by assuming two possible pathways: (1) nucleophilic attack of hydroxide ion on the car-bony1 carbon to give a tetrahedral complex followed by its breakdown to carbamic acid (BA,~); and (2) proton abstraction by hydroxide ion at the nitrogen atom followed by elimination of the alkoxide ion to form N-methyl isocyanate (ElcB). Reaction coordinate analysis showed that the reaction mechanism is determined by both the stability of an intermediate and the energy barrier for elimination.

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