Journal article
The E2C mechanism in elimination reactions. IX. Re-examination of the olefin-like transition-state
Australian Journal of Chemistry, Vol.36(9), pp.1667-1673
1983
Abstract
The kinetics and product olefins arising from E2C-like elimination reactions of secondary bromides and tosylates having various alkyl and conjugating substituents at Cα and Cβ are re-examined in the light of the theoretical Pross-Shaik valence-bond model and the apparent lack of a β-phenyl effect. Comparison of the effect of substituents at Cα and Cβ shows that whilst there are differences in reactivity and products of E2C reactions there is also a large degree of double-bond character in the transition state. There is a good correlation between the kinetics of E2C reactions and the double-bond stabilization energy arising from both alkyl and conjugating substituents. Contributing valence-bond structures, giving asymmetry and partial charge at Cα and Cβ appear to vary in importance according to leaving group and substituent type.
Details
- Title
- The E2C mechanism in elimination reactions. IX. Re-examination of the olefin-like transition-state
- Authors/Creators
- D.M. Muir (Author/Creator)A.J. Parker (Author/Creator)
- Publication Details
- Australian Journal of Chemistry, Vol.36(9), pp.1667-1673
- Publisher
- Commonwealth Scientific and Industrial Research Organization Publishing
- Identifiers
- 991005540723307891
- Copyright
- © 1983 CSIRO
- Murdoch Affiliation
- School of Mathematical and Physical Sciences
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.824 Solvolysis
- Web Of Science research areas
- Chemistry, Multidisciplinary
- ESI research areas
- Chemistry