Theoretical study of the alkaline hydrolysis of a bicyclic Aza-b-lactam

Show simple item record Coll, Miguel Frau Munar, Juan Vilanova Canet, Bartolomé Donoso Pardo, Josefa Laurentina Muñoz Izquierdo, Francisco García Blanco, Francisco 2018-10-23T11:15:35Z
dc.description.abstract [eng] Various mechanisms for the alkaline hydrolysis of an aza-â-lactam in the gas phase were studied by ab initio calculations at the RHF/6-31+G*//RHF/6-31+G*, MP2/6-31+G*//MP2/6-31+G*, and B3LYP/6-31+G*//B3LYP/6-31+G* levels. Solvent effects were considered via IPCM (isodensity polarizable continuum model) calculations at the IPCM/6-31+G*//RHF/6-31+G* level. The alkaline hydrolysis of beta-lactams begins with a nucleophilic attack of the hydroxyl ion on the carbonyl of the â-lactam ring. The tetrahedral intermediate thus formed undergoes cleavage of the C7-N4 bond to give the reaction end products. In addition to the typical cleavage reaction, the â-lactam studied can undergo opening at the C7-N6 bond (Scheme 1). Both processes have a similar activation energy that varies slightly depending on the particular computation method used. The most stable end products are those formed via the typical mechanism. In any case, both mechanisms yield products possessing a carbamate group, which suggests that the starting aza-â-lactam might be an effective inhibitor for beta-lactamases
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a:
dc.relation.ispartof Journal of Physical Chemistry, 2000, vol. 104, num. 47, p. 11389-11394
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Theoretical study of the alkaline hydrolysis of a bicyclic Aza-b-lactam
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion 2018-10-23T11:15:35Z info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess

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