PM3 semi-empirical study of stereoelectronic effects in the Baeyer–Villiger reaction

The Baeyer–Villiger reaction of polymethoxybenzaldehydes with peroxysuccinic acid (PSA) is studied theoretically. The semi-empirical SCF-MO/PM3 method has been used to study the reaction and to calculate the energy profiles. In addition, heat of formation computations and bond order analyses of the...

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Bibliographic Details
Published in:Journal of molecular structure. Theochem 1998-08, Vol.434 (1), p.183-191
Main Authors: Hannachi, Hedi, Anoune, Naoual, Arnaud, Christian, Lantéri, Pierre, Longeray, Rémi, Chermette, Henry
Format: Article
Language:English
Subjects:
Baeyer–Villiger reaction
Bond order
Catalysis
Chemical Sciences
PM3
Reaction coordinate
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Summary:The Baeyer–Villiger reaction of polymethoxybenzaldehydes with peroxysuccinic acid (PSA) is studied theoretically. The semi-empirical SCF-MO/PM3 method has been used to study the reaction and to calculate the energy profiles. In addition, heat of formation computations and bond order analyses of the transition species along the reaction coordinates have been performed and are interpreted qualitatively in terms of electron flow through the system during aryl migration. Our results support the hypothesis that the second step is a concerted reaction. Our data support a definite effect of the substituent on the aryl migration. The theoretical predictions are in good agreement with experimental results.
ISSN:0166-1280
1872-7999
DOI:10.1016/S0166-1280(98)00096-7