Journal article
Dehydrohalogenation of ethyl halide
Tetrahedron Letters, Vol.55(35), pp.4860-4868
2014
Abstract
Unimolecular decomposition kinetics of selected ethyl halides, phenethyl halides and methoxyphenethyl halides have been investigated using high level computational chemistry methods. The phenethyl halides decompose faster than the ethyl halides due to a more electronegative chlorine atom, induced by the chloroethyl functionality as an electron-withdrawing group. 1-Chloro-2-(methylthio)ethane exhibits faster dehydrochlorination than that of chloroethane/1-chloro-2-methoxyethane, owing to more polarisable C⋯H and C⋯Cl bonds in the transition structures. Calculations suggest that electronic factors rather than anchimeric assistance influence the dehydrochlorination reactions.
Details
- Title
- Dehydrohalogenation of ethyl halide
- Authors/Creators
- N. Ahubelem (Author/Creator) - University of Newcastle AustraliaM. Altarawneh (Author/Creator) - Murdoch UniversityB.Z. Dlugogorski (Author/Creator) - Murdoch University
- Publication Details
- Tetrahedron Letters, Vol.55(35), pp.4860-4868
- Publisher
- Elsevier BV
- Identifiers
- 991005540598407891
- Copyright
- 2014 Elsevier Ltd
- Murdoch Affiliation
- School of Engineering and Information Technology
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
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- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.2278 Heterocyclic Synthesis Mechanisms
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry