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

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Yeguas, Violeta López, Ramón Díaz, Natalia Campomanes, Pablo
Description	Author Affiliation: Yeguas V ( Departamento de Química Física y Analítica, Universidad de Oviedo, C/Julián Clavería, 8, 33006, Oviedo, Spain.)
Abstract	Computations on the reaction of azetidin-2-one , N-sulfonate azetidin-2-one, and 3-formylamine-N-sulfonate azetidin-2-one with $[Mo(OH)(η^{3}-C_{3}H_{5})(CO)_{2}(N_{2}C_{2}H_{4})]$ 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.
ISSN	14779226
Issue Number	45
e-ISSN	13645447
Journal	Dalton Trans.
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2008-12-07
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Azetidines Chemical Synthesis Molybdenum Chemistry Organometallic Compounds Indicators And Reagents Models, Molecular Molecular Conformation Journal Article Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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