The energetic advantage of 5-exo versus 6-endo epoxide openings: a preference overwhelmed by antibody catalysis

In order to calculate the energy difference between 5-exo and 6-endo epoxide openings, we have carried out ab initio calculations to locate the transition structures for both processes. Our model calculations were carried out with hydrogen in place of the benzyl group present. Geometries were comple...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1993-09, Vol.115 (18), p.8453-8454
Main Authors: Na, Jim, Houk, K. N, Shevlin, Charles G, Janda, Kim D, Lerner, Richard A
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Summary:In order to calculate the energy difference between 5-exo and 6-endo epoxide openings, we have carried out ab initio calculations to locate the transition structures for both processes. Our model calculations were carried out with hydrogen in place of the benzyl group present. Geometries were completely optimized, and transition states were characterized by harmonic frequency analysis.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00071a067