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:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - 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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Reaction thermochemistry data
Go To: Top, 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
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Individual Reactions
C9H9- + =
By formula: C9H9- + H+ = C9H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 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 |
| ΔrH° | 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 |
| ΔrG° | 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 |
| ΔrG° | 1513. ± 19. | kJ/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B |
=
By formula: C9H10 = C9H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.3 ± 0.6 | kJ/mol | Eqk | Taskinen and Lindholm, 1994 | liquid phase; solvent: DMSO; Heat of isomerization; ALS |
+
=
By formula: H2 + C9H10 = C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -126. ± 0.8 | kJ/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Hydrocarbon; ALS |
=
By formula: C9H10 = C9H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -23.3 ± 0.5 | kJ/mol | Eqk | Taskinen and Lindholm, 1994 | liquid phase; solvent: DMSO; ALS |
=
By formula: C9H10 = C9H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -20.1 | kJ/mol | Eqk | Taskinen and Lindholm, 1994 | gas phase; Heat of isomerization; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
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
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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