Benzene, 2-propenyl-
- Formula: C9H10
- Molecular weight: 118.1757
- 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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Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1235.5 | kcal/mol | Ccb | Clopatt, 1932 | Corresponding ΔfHºliquid = 47.5 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 429. ± 2. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 233.15 | K | N/A | Lespieau, 1930 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.1 ± 0.05 | kcal/mol | GS | Verevkin, 1999 | Based on data from 274. to 313. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.1 ± 0.05 | 294. | GS | Verevkin, 1999 | Based on data from 274. to 313. K.; AC |
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- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 368.1 ± 2.2 | kcal/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° | 368.1 ± 4.6 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 361.5 ± 2.1 | kcal/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° | 361.5 ± 4.5 | kcal/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° | -2.9 ± 0.1 | kcal/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° | -30.2 ± 0.2 | kcal/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Hydrocarbon; ALS |
By formula: C9H10 = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -5.6 ± 0.1 | kcal/mol | Eqk | Taskinen and Lindholm, 1994 | liquid phase; solvent: DMSO; ALS |
By formula: C9H10 = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.80 | kcal/mol | Eqk | Taskinen and Lindholm, 1994 | gas phase; Heat of isomerization; ALS |
Gas phase ion energetics 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C9H10+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.70 | PE | Fu and Dunbar, 1978 | LLK |
7.8 ± 0.1 | EI | Koppel, Schwarz, et al., 1974 | LLK |
8.60 | PE | Rabalais and Colton, 1973 | LLK |
8.20 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
9.16 | PE | Eaton and Traylor, 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C9H9+ | 11.6 ± 0.1 | H | EI | Koppel, Schwarz, et al., 1974 | LLK |
De-protonation reactions
C9H9- + =
By formula: C9H9- + H+ = C9H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 368.1 ± 2.2 | kcal/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° | 368.1 ± 4.6 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 361.5 ± 2.1 | kcal/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° | 361.5 ± 4.5 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B |
IR Spectrum
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Lespieau, 1930
Lespieau, R.,
Preparation of the β Dibromides of Trimethylenic Hydrocarbons,
Bull. Soc. Chim. Fr., 1930, 47, 847. [all data]
Verevkin, 1999
Verevkin, Sergey P.,
Thermochemical investigation on α-methyl-styrene and parent phenyl substituted alkenes,
Thermochimica Acta, 1999, 326, 1-2, 17-25, https://doi.org/10.1016/S0040-6031(98)00585-1
. [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]
Fu and Dunbar, 1978
Fu, E.W.; Dunbar, R.C.,
Photodissociation spectroscopy and structural rearrangements in ions of cyclooctatetraene, styrene and related molecules,
J. Am. Chem. Soc., 1978, 100, 2283. [all data]
Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F.,
Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VIII. Struktur der stabilen und instabilen ionen[C9H9]+ aus isomeren C9H10- kohlenwasserstoffen,
Org. Mass Spectrom., 1974, 8, 25. [all data]
Rabalais and Colton, 1973
Rabalais, J.W.; Colton, R.J.,
Electronic interaction between the phenyl group and its unsaturated substituents,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]
Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G.,
Distortional stabilization in phenyl participations,
J. Am. Chem. Soc., 1974, 96, 7109. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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