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

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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Veröffentlicht in:Journal of the American Chemical Society 1993-09, Vol.115 (18), p.8453-8454
Hauptverfasser: Na, Jim, Houk, K. N, Shevlin, Charles G, Janda, Kim D, Lerner, Richard A
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Exact sciences and technology
Kinetics and mechanisms
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Reactivity and mechanisms
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container_end_page 8454
container_issue 18
container_start_page 8453
container_title Journal of the American Chemical Society
container_volume 115
creator Na, Jim
Houk, K. N
Shevlin, Charles G
Janda, Kim D
Lerner, Richard A
description 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.
doi_str_mv 10.1021/ja00071a067
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subjects Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
title The energetic advantage of 5-exo versus 6-endo epoxide openings: a preference overwhelmed by antibody catalysis
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