Benzeneacetic acid
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChIKey: WLJVXDMOQOGPHL-UHFFFAOYSA-N
- CAS Registry Number: 103-82-2
- 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: Acetic acid, phenyl-; α-Toluic acid; Benzenacetic acid; Phenylacetic acid; ω-Phenylacetic acid; Phenylethanoic acid; Kyselina fenyloctova; 2-Phenylacetic acid; NSC 125718
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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°solid | -3896.7 ± 0.80 | kJ/mol | Ccb | Wrede, 1911 | Corresponding ΔfHºsolid = -394.7 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -3897. | kJ/mol | Ccb | Auwers and Roth, 1910 | Corresponding ΔfHºsolid = -394. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -3905. | kJ/mol | Ccb | Fischer and Wrede, 1904 | Heat of combustion corrected for pressure; Corresponding ΔfHºsolid = -386. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -3910. | kJ/mol | Ccb | Lemoult, 1904 | Corresponding ΔfHºsolid = -381. kJ/mol (simple calculation by NIST; no Washburn corrections) |
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 by: John E. Bartmess
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
C8H7O2- + =
By formula: C8H7O2- + H+ = C8H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1429. ± 8.8 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase |
ΔrH° | 1427. ± 8.8 | kJ/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1400. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase |
ΔrG° | 1398. ± 8.4 | kJ/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale |
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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H8O2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.26 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
~8.26 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
8.26 | PE | Meeks, Wahlborg, et al., 1981 | LLK |
8.72 | PE | Klasinc, Kovac, et al., 1983 | Vertical value; LBLHLM |
9.1 | PE | Meeks, Wahlborg, et al., 1981 | Vertical value; LLK |
De-protonation reactions
C8H7O2- + =
By formula: C8H7O2- + H+ = C8H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1429. ± 8.8 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrH° | 1427. ± 8.8 | kJ/mol | G+TS | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1400. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
ΔrG° | 1398. ± 8.4 | kJ/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wrede, 1911
Wrede, F.,
Uber die Bestimmung von Berbrennungswarmen mittels der kalorimetrischen Bombe unter Benutzung des Platinwiderstandsthermometers,
Z. Phys. Chem. (Leipzig), 1911, 81-94. [all data]
Auwers and Roth, 1910
Auwers, K.; Roth, W.A.,
Thermochemische Untersuchungen. I. Uber Beziehungen zwischen Konstitution und Verbrennungswarme ungesattigter Verbindungen,
Justus Liebigs Ann. Chem., 1910, 239-248. [all data]
Fischer and Wrede, 1904
Fischer, E.; Wrede, F.,
Uber die Verbrennungswarme einiger organischer Verbindungen,
Sitzungsber. Dtsch. Akad. Wiss. Berlin Kl. Math. Phys. Tech., 1904, 687-715. [all data]
Lemoult, 1904
Lemoult, M.P.,
Remarques sur une serie recenie de determinations calorimetriques,
Compt. Rend., 1904, 663-635. [all data]
Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P.,
Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria,
Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092
. [all data]
Jinfeng, Topsom, et al., 1988
Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S.,
Acidities of Substituted Acetic Acids,
J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X
. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Meeks, Wahlborg, et al., 1981
Meeks, J.; Wahlborg, A.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives,
J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔcH°solid Enthalpy of combustion of solid at standard conditions 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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