Issue 45, 2008

Ring opening at N1–C2 bond of azetidin-2-ones by a molybdenum hydroxo-carbonyl complex: evidence from a computational study

Abstract

Computations on the reaction of azetidin-2-one, N-sulfonate azetidin-2-one, and 3-formylamine-N-sulfonate azetidin-2-one with [Mo(OH)(η3-C3H5)(CO)2(N2C2H4)] were performed at the B3LYP/6-31 + G(d,p) (LANL2DZ for Mo augmented by f polarization functions with exponents 1.043) taking into account solvent effects by means of the PCM-UAHF model. According to our calculations, the rate-determining energy barrier for the azetidin-2-one case, 38.0 kcal mol−1, becomes 28.8 and 26.1 kcal mol−1 for the N-sulfonate azetidin-2-one and 3-formylamine-N-sulfonate azetidin-2-one ones, respectively. The presence of the sulfonate group is crucial to cleave the β-lactam N1–C2 bond by the Mo complex thanks to the interaction of the sulfonate group with the hydroxyl and bidentate ligands of the complex. This could be of interest for the synthesis of β-amino acids and their derivatives from β-lactams in mild conditions and low polarity solvents promoted by organometallic complexes.

Graphical abstract: Ring opening at N1–C2 bond of azetidin-2-ones by a molybdenum hydroxo-carbonyl complex: evidence from a computational study

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2008
Accepted
12 Aug 2008
First published
08 Oct 2008

Dalton Trans., 2008, 6427-6434

Ring opening at N1–C2 bond of azetidin-2-ones by a molybdenum hydroxo-carbonyl complex: evidence from a computational study

V. Yeguas, N. Díaz, P. Campomanes and R. López, Dalton Trans., 2008, 6427 DOI: 10.1039/B810868D

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