Benzene, 2-propenyl-

Formula: C₉H₁₀
Molecular weight: 118.1757
IUPAC Standard InChI: InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-5,7-8H,1,6H2
IUPAC Standard InChIKey: HJWLCRVIBGQPNF-UHFFFAOYSA-N
CAS Registry Number: 300-57-2
Chemical structure:
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Other names: Benzene, allyl-; Allylbenzene; 1-Phenyl-2-propene; 1-Propene, 3-phenyl-; 2-Propenylbenzene; 3-Phenyl-1-propene; 3-Phenylpropene
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Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5169.3	kJ/mol	Ccb	Clopatt, 1932	Corresponding Δ_fHº_liquid = 199. kJ/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

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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

C₉H₉^- + = Benzene, 2-propenyl-

By formula: C₉H₉^- + H⁺ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1540. ± 9.2	kJ/mol	G+TS	Glasovac, Eckert-Maksic, et al., 2002	gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Δ_rH°	1540. ± 19.	kJ/mol	G+TS	Dahlke and Kass, 1991	gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1513. ± 8.8	kJ/mol	IMRE	Glasovac, Eckert-Maksic, et al., 2002	gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Δ_rG°	1513. ± 19.	kJ/mol	IMRB	Dahlke and Kass, 1991	gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B

Benzene, 2-propenyl- =

By formula: C₉H₁₀ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.3 ± 0.6	kJ/mol	Eqk	Taskinen and Lindholm, 1994	liquid phase; solvent: DMSO; Heat of isomerization; ALS

+ Benzene, 2-propenyl- =

By formula: H₂ + C₉H₁₀ = C₉H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-126. ± 0.8	kJ/mol	Chyd	Rogers and McLafferty, 1971	liquid phase; solvent: Hydrocarbon; ALS

Benzene, 2-propenyl- =

By formula: C₉H₁₀ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-23.3 ± 0.5	kJ/mol	Eqk	Taskinen and Lindholm, 1994	liquid phase; solvent: DMSO; ALS

= Benzene, 2-propenyl-

By formula: C₉H₁₀ = C₉H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-20.1	kJ/mol	Eqk	Taskinen and Lindholm, 1994	gas phase; Heat of isomerization; ALS

References

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Clopatt, 1932
Clopatt, J.A., Eine neue Methode zur Bestimmung der Verbrennungswarme fluchtiger Stoffe, Soc. Scient. Fenn. Commentat. Phys. Math., 1932, 6, 1-15. [all data]

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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Symbols used in this document:

Δ_cH°_liquid Enthalpy of combustion of liquid at standard conditions

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions