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Ab initio study of β-lactam compounds: acidic hydrolysis

Authors
Journal
Journal of Molecular Structure THEOCHEM
0166-1280
Publisher
Elsevier
Publication Date
Volume
426
Identifiers
DOI: 10.1016/s0166-1280(97)00333-3
Keywords
  • Ab Initio
  • β-Lactam Compounds
  • Acidic Hydrolysis

Abstract

Abstract A complete study on the acidic hydrolysis of the azetidin-2-one ring, an essential component of β-lactam compounds, has been carried out by means of ab initio calculations by using a 6–31G ∗∗ type basis set. The former reaction has been studied by means of an A-1 type unimolecular mechanism, characterized by an N-protonation followed by an opening of the ring and further addition of water to the carbonyl group. The system involving the azetidin-2-one ring, the H 3O + ion and a water molecule has been considered, where three transition states have been identified, being the barriers corresponding to the addition of H + to the nitrogen and the addition of water to the carbonyl group being practically negligible (first and third reaction steps, respectively). The energy barrier for the opening of the ring (second reaction step) was 14.23 kcal mol −1.

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