TY - JOUR
T1 - Dehydrohalogenation of ethyl halides
AU - Ahubelem, Nwakamma
AU - Altarawneh, Mohammednoor
AU - Dlugogorski, Bogdan Z.
N1 - Funding Information:
This study was supported by the Australian Research Council (ARC) and a grant of computing time from The National Computational Infrastructure (NCI), Australia. N.A. thanks The University of Newcastle, Australia for a postgraduate research scholarship.
Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
KW - Activation enthalpy
KW - Anchimeric assistance
KW - Arrhenius parameters
KW - Dehydrohalogenation
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U2 - 10.1016/j.tetlet.2014.07.009
DO - 10.1016/j.tetlet.2014.07.009
M3 - Article
AN - SCOPUS:84906079227
VL - 55
SP - 4860
EP - 4868
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 35
ER -