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Mechanisms of hydrolysis of salicylanilide N-methylcarbamates

โœ Scribed by Leo W. Brown; S. P. Richard Hsi; Arlington A. Forist


Book ID
102408309
Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
291 KB
Volume
63
Category
Article
ISSN
0022-3549

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๐Ÿ“œ SIMILAR VOLUMES


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โœ Leo W. Brown; Arlington A. Forist ๐Ÿ“‚ Article ๐Ÿ“… 1972 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 351 KB

The kinetics of hydrolysis of the carbamoyl group in salicylanilide N-methylcarbamate (I) and 4-biphenylyl N-methylcarbamate (11) showed that the reaction was first order with respect to both hydroxide ion and carbamate. At 37", the hydroxideion-catalyzed hydrolysis of 1 to yield salicylanilide (111

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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) prot