Benzeneacetic acid
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChI: InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
- 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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Gas phase ion energetics 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 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° | 341.5 ± 2.1 | kcal/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrH° | 341.1 ± 2.1 | kcal/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° | 334.5 ± 2.0 | kcal/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| ΔrG° | 334.1 ± 2.0 | kcal/mol | IMRE | Jinfeng, Topsom, et al., 1988 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, 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.
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]
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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy 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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