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Allyl chloride

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Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C3H4Cl- + Hydrogen cation = Allyl chloride

By formula: C3H4Cl- + H+ = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar1590. ± 17.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1571. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B
Quantity Value Units Method Reference Comment
Deltar1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B

Allyl chloride + 2Dimethylamine = N-Allyl-N,N-dimethylamine + Dimethylamine hydrochloride

By formula: C3H5Cl + 2C2H7N = C5H11N + C2H8ClN

Quantity Value Units Method Reference Comment
Deltar-82.6 ± 0.4kJ/molCmBeldie, Aelenei, et al., 1982liquid phase; ALS

Allyl chloride = 1-Propene, 1-chloro-

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar-9.96 ± 0.42kJ/molCisoAbell and Adolf, 1969gas phase; HBr catalyst; ALS

1-Propene, 1-chloro-, (Z)- = Allyl chloride

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar15. ± 0.8kJ/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

1-Propene, 1-chloro- = Allyl chloride

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar11. ± 0.8kJ/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Beldie, Aelenei, et al., 1982
Beldie, C.; Aelenei, N.; Onu, A.; Nemtoi, G., Thermochemical characterization of the reactions involved in the allyldimethylamine synthesis, Rev. Chim. (Bucharest), 1982, 33, 917-919. [all data]

Abell and Adolf, 1969
Abell, P.I.; Adolf, P.K., HBr catalyzed photoisomerization of allyl halides, J. Chem. Thermodyn., 1969, 1, 333-338. [all data]

Alfassi, Golden, et al., 1973
Alfassi, Z.B.; Golden, D.M.; Benson, S.W., 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, J. Chem. Thermodyn., 1973, 5, 411-420. [all data]


Notes

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