The mechanistic criterion of reversed substituent effects in reactions, formally classified as 5-endo-trig and 6-endo-trig, is examined.
Enthalpy and Entropy in Ring Closure Reactions
β Scribed by Felice C. Lightstone; Thomas C. Bruice
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- English
- Weight
- 228 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0045-2068
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β¦ Synopsis
The strain and entropy effects of the lactone formation from ΝΆ-bromoalkane-carboxylate ions in ring sizes 3 to 23 is reevaluated. We find that β¬H β‘ is the largest contributor to the observed rates (β¬G β‘ ) for ring sizes 3 to 6, while ΟͺT β¬S β‘ has little influence, ΟͺT β¬S β‘ has more effect on the observed rates for ring sizes 8 and larger.
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