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1-Propene, 3-iodo-

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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Individual Reactions

Hydrogen iodide + 1-Propene, 3-iodo- = Propene + Iodine

By formula: HI + C3H5I = C3H6 + I2

Quantity Value Units Method Reference Comment
Deltar-7.96 ± 0.33kcal/molEqkRodgers, Golden, et al., 1966gas phase; ALS
Deltar-9.5 ± 1.0kcal/molEqkRodgers, Golden, et al., 1966gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -8.33 ± 0.23 kcal/mol; At 527 K; ALS

C3H4I- + Hydrogen cation = 1-Propene, 3-iodo-

By formula: C3H4I- + H+ = C3H5I

Quantity Value Units Method Reference Comment
Deltar370.7 ± 2.1kcal/molG+TSPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B
Quantity Value Units Method Reference Comment
Deltar363.4 ± 2.0kcal/molIMRBPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B

1-Propene, 3-iodo- + Water = Hydrogen iodide + 2-Propen-1-ol

By formula: C3H5I + H2O = HI + C3H6O

Quantity Value Units Method Reference Comment
Deltar-2.10kcal/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

(E)-1-Iodo-1-propene = 1-Propene, 3-iodo-

By formula: C3H5I = C3H5I

Quantity Value Units Method Reference Comment
Deltar-0.4kcal/molEqkAlfassi, Golden, et al., 1973gas phase; ALS

(Z)-1-Iodo-1-propene = 1-Propene, 3-iodo-

By formula: C3H5I = C3H5I

Quantity Value Units Method Reference Comment
Deltar1.2kcal/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.

Rodgers, Golden, et al., 1966
Rodgers, A.S.; Golden, D.M.; Benson, S.W., The thermochemistry of the gas phase equilibrium I2 + C3H6 = C3H5I + HI, J. Am. Chem. Soc., 1966, 88, 3194-3196. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

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]

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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