1-Propene, 3-bromo-

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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

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Individual Reactions

C3H4Br- + Hydrogen cation = 1-Propene, 3-bromo-

By formula: C3H4Br- + H+ = C3H5Br

Quantity Value Units Method Reference Comment
Δr1570. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B
Quantity Value Units Method Reference Comment
Δr1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B

1-Propene, 3-bromo- + Water = Hydrogen bromide + 2-Propen-1-ol

By formula: C3H5Br + H2O = HBr + C3H6O

Quantity Value Units Method Reference Comment
Δr-15.kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

1-Propene, 3-bromo- = 1-Propene, 1-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr-3.0 ± 0.4kJ/molCisoAbell and Adolf, 1969gas phase; HBr catalyst; ALS

(E)-1-Bromo-1-propene = 1-Propene, 3-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr1.3 ± 0.50kJ/molEqkAlfassi, Golden, et al., 1973gas phase; ALS

(Z)-1-Bromo-1-propene = 1-Propene, 3-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr4.5 ± 0.4kJ/molEqkAlfassi, Golden, et al., 1973gas phase; ALS

References

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

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]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [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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