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Benzene, 2-propenyl-

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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

C9H9- + Hydrogen cation = Benzene, 2-propenyl-

By formula: C9H9- + H+ = C9H10

Quantity Value Units Method Reference Comment
Deltar368.1 ± 2.2kcal/molG+TSGlasovac, Eckert-Maksic, et al., 2002gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Deltar368.1 ± 4.6kcal/molG+TSDahlke and Kass, 1991gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B
Quantity Value Units Method Reference Comment
Deltar361.5 ± 2.1kcal/molIMREGlasovac, Eckert-Maksic, et al., 2002gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Deltar361.5 ± 4.5kcal/molIMRBDahlke and Kass, 1991gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B

Benzene, 2-propenyl- = (Z)-1-Phenylpropene

By formula: C9H10 = C9H10

Quantity Value Units Method Reference Comment
Deltar-2.9 ± 0.1kcal/molEqkTaskinen and Lindholm, 1994liquid phase; solvent: DMSO; Heat of isomerization; ALS

Hydrogen + Benzene, 2-propenyl- = Benzene, propyl-

By formula: H2 + C9H10 = C9H12

Quantity Value Units Method Reference Comment
Deltar-30.2 ± 0.2kcal/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS

Benzene, 2-propenyl- = trans-β-Methylstyrene

By formula: C9H10 = C9H10

Quantity Value Units Method Reference Comment
Deltar-5.6 ± 0.1kcal/molEqkTaskinen and Lindholm, 1994liquid phase; solvent: DMSO; ALS

trans-β-Methylstyrene = Benzene, 2-propenyl-

By formula: C9H10 = C9H10

Quantity Value Units Method Reference Comment
Deltar-4.80kcal/molEqkTaskinen and Lindholm, 1994gas phase; Heat of isomerization; 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.

Glasovac, Eckert-Maksic, et al., 2002
Glasovac, Z.; Eckert-Maksic, M.; Dacres, J.E.; Kass, S.R., Gas phase formation of 1-phenylcyclobuten-3-yl and 1- phenylallyl anions and a determination of the allylic C-H acidities and bond dissociation energies of 1-phenylcyclobutene and (E)-1-phen, J. Chem. Soc. Perkin Trans., 2002, 2, 3, 410-415, https://doi.org/10.1039/b111398d . [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]

Taskinen and Lindholm, 1994
Taskinen, E.; Lindholm, N., Relative thermodynamic stabilities of the isomeric propenylbenzenes, J. Phys. Org. Chem., 1994, 7, 256-258. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]


Notes

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