The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group

Ze'ev B. Alfassi; David M. Golden; Sidney W. Benson

doi:10.1016/S0021-9614(73)80032-1

The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the C_d-(H)(X) group

Ze'ev B. Alfassi, David M. Golden, Sidney W. Benson

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

The equilibrium constants for the isomerization of allyl chloride to cis- and trans-1-chloro-1-propene have been studied at 573 to 651 K. The reaction was catalyzed by either I₂ or a mixture of (HBr+5 mass per cent Br₂): From these results the enthalpy of formation of 1-chloro-1-propene has been calculated (cis = -1.8, trans = -1.1 kcal_th mol^-1). The thermodynamic properties of the different allyl halides and 1-halo-1-propenes are discussed and the values of the contributions of the C_d-(H) (X) and C-(C_d) (H)₂ (X) groups to the enthalpy of formation and entropy are calculated. It is suggested that the enthalpy of formation of vinyl chloride is actually (5.0±1.0) kcal_th mol^-1, rather than the currently accepted value of 8.4 kcal_th mol^-1.

Original language	English
Pages (from-to)	411-420
Number of pages	10
Journal	Journal of Chemical Thermodynamics
Volume	5
Issue number	3
DOIs	https://doi.org/10.1016/S0021-9614(73)80032-1
State	Published - 1 Jan 1973
Externally published	Yes

ASJC Scopus subject areas

Atomic and Molecular Physics, and Optics
General Materials Science
Physical and Theoretical Chemistry

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@article{de0687a9c8764cc4b2ec8b122d92f4a0,

title = "The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group",

abstract = "The equilibrium constants for the isomerization of allyl chloride to cis- and trans-1-chloro-1-propene have been studied at 573 to 651 K. The reaction was catalyzed by either I2 or a mixture of (HBr+5 mass per cent Br2): From these results the enthalpy of formation of 1-chloro-1-propene has been calculated (cis = -1.8, trans = -1.1 kcalth mol-1). The thermodynamic properties of the different allyl halides and 1-halo-1-propenes are discussed and the values of the contributions of the Cd-(H) (X) and C-(Cd) (H)2 (X) groups to the enthalpy of formation and entropy are calculated. It is suggested that the enthalpy of formation of vinyl chloride is actually (5.0±1.0) kcalth mol-1, rather than the currently accepted value of 8.4 kcalth mol-1.",

author = "Alfassi, {Ze'ev B.} and Golden, {David M.} and Benson, {Sidney W.}",

note = "Funding Information: a This work was supported in part by Grant No. 00353-08 of the Environmental Protection Agency, Air Pollution Control Administration. Postdoctoral Research Associate. Present address: Faculty of Sciences, University of the Negev, Beer Sheva, Israel.",

year = "1973",

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doi = "10.1016/S0021-9614(73)80032-1",

language = "English",

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T1 - The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group

AU - Alfassi, Ze'ev B.

AU - Golden, David M.

AU - Benson, Sidney W.

N1 - Funding Information: a This work was supported in part by Grant No. 00353-08 of the Environmental Protection Agency, Air Pollution Control Administration. Postdoctoral Research Associate. Present address: Faculty of Sciences, University of the Negev, Beer Sheva, Israel.

PY - 1973/1/1

Y1 - 1973/1/1

N2 - The equilibrium constants for the isomerization of allyl chloride to cis- and trans-1-chloro-1-propene have been studied at 573 to 651 K. The reaction was catalyzed by either I2 or a mixture of (HBr+5 mass per cent Br2): From these results the enthalpy of formation of 1-chloro-1-propene has been calculated (cis = -1.8, trans = -1.1 kcalth mol-1). The thermodynamic properties of the different allyl halides and 1-halo-1-propenes are discussed and the values of the contributions of the Cd-(H) (X) and C-(Cd) (H)2 (X) groups to the enthalpy of formation and entropy are calculated. It is suggested that the enthalpy of formation of vinyl chloride is actually (5.0±1.0) kcalth mol-1, rather than the currently accepted value of 8.4 kcalth mol-1.

AB - The equilibrium constants for the isomerization of allyl chloride to cis- and trans-1-chloro-1-propene have been studied at 573 to 651 K. The reaction was catalyzed by either I2 or a mixture of (HBr+5 mass per cent Br2): From these results the enthalpy of formation of 1-chloro-1-propene has been calculated (cis = -1.8, trans = -1.1 kcalth mol-1). The thermodynamic properties of the different allyl halides and 1-halo-1-propenes are discussed and the values of the contributions of the Cd-(H) (X) and C-(Cd) (H)2 (X) groups to the enthalpy of formation and entropy are calculated. It is suggested that the enthalpy of formation of vinyl chloride is actually (5.0±1.0) kcalth mol-1, rather than the currently accepted value of 8.4 kcalth mol-1.

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VL - 5

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JO - Journal of Chemical Thermodynamics

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ER -

The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the C_d-(H)(X) group

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