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.
Original language | English |
---|---|
Pages (from-to) | 4860-4868 |
Number of pages | 9 |
Journal | Tetrahedron Letters |
Volume | 55 |
Issue number | 35 |
DOIs | |
Publication status | Published - 2014 |
Externally published | Yes |
Keywords
- Activation enthalpy
- Anchimeric assistance
- Arrhenius parameters
- Dehydrohalogenation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry