Dehydrohalogenation of ethyl halides

Nwakamma Ahubelem; Mohammednoor Altarawneh; Bogdan Z. Dlugogorski

doi:10.1016/j.tetlet.2014.07.009

Dehydrohalogenation of ethyl halides

Nwakamma Ahubelem, Mohammednoor Altarawneh, Bogdan Z. Dlugogorski

Research output: Contribution to journal › Article

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	https://doi.org/10.1016/j.tetlet.2014.07.009
Publication status	Published - 27 Aug 2014
Externally published	Yes

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10.1016/j.tetlet.2014.07.009

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title = "Dehydrohalogenation of ethyl halides",

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.",

keywords = "Activation enthalpy, Anchimeric assistance, Arrhenius parameters, Dehydrohalogenation",

author = "Nwakamma Ahubelem and Mohammednoor Altarawneh and Dlugogorski, {Bogdan Z.}",

year = "2014",

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doi = "10.1016/j.tetlet.2014.07.009",

language = "English",

volume = "55",

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journal = "Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry",

issn = "0040-4039",

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TY - JOUR

T1 - Dehydrohalogenation of ethyl halides

AU - Ahubelem, Nwakamma

AU - Altarawneh, Mohammednoor

AU - Dlugogorski, Bogdan Z.

PY - 2014/8/27

Y1 - 2014/8/27

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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DO - 10.1016/j.tetlet.2014.07.009

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JO - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

JF - Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry

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