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Theoretical Study of the Alkaline Hydrolysis of Tricyclic Carbapenem
Author(s) -
Fasoli Hector J.,
Frau Juan
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590054
Subject(s) - chemistry , alkaline hydrolysis , hydrolysis , cephalosporin , tricyclic , lactam , reactivity (psychology) , combinatorial chemistry , organic chemistry , medicinal chemistry , antibiotics , biochemistry , medicine , alternative medicine , pathology
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.