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Allyl chloride

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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-1.3kcal/molIonTraeger, 1984 

Condensed phase 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 by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
29.90298.von Reis, 1881T = 289 to 334 K.

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

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
Deltar379.9 ± 4.1kcal/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar375.4 ± 2.1kcal/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B
Quantity Value Units Method Reference Comment
Deltar372.5 ± 4.0kcal/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar368.0 ± 2.0kcal/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-19.74 ± 0.09kcal/molCmBeldie, Aelenei, et al., 1982liquid phase; ALS

Allyl chloride = 1-Propene, 1-chloro-

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar-2.38 ± 0.10kcal/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
Deltar3.5 ± 0.2kcal/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

1-Propene, 1-chloro- = Allyl chloride

By formula: C3H5Cl = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar2.6 ± 0.2kcal/molEqkAlfassi, Golden, et al., 1973liquid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259-271. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References