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
Theoretical Study of the Alkaline Hydrolysis of Tricyclic Carbapenem
✍ Scribed by Hector J. Fasoli; Juan Frau
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- German
- Weight
- 82 KB
- Volume
- 88
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Alkaline hydrolysis is a good test to evaluate the properties of β‐lactam compounds and derivatives. In this work, a RHF/6‐31+G*//RHF/6‐31+G* theoretical study of the mechanism controlling the alkaline hydrolysis of sanfetrinem was conducted. The geometric properties of this compound are consistent with an intrinsic reactivity similar to that of other β‐lactams including penicillins and cephalosporins. Also, similarly to cephalosporins, the MeO group provides an alternative route for the hydrolysis mechanism.
📜 SIMILAR VOLUMES
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 sub