Benzoic acid
- Formula: C7H6O2
- Molecular weight: 122.1213
- IUPAC Standard InChI: InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
- IUPAC Standard InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-N
- CAS Registry Number: 65-85-0
- 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: Benzenecarboxylic acid; Benzeneformic acid; Benzenemethanoic acid; Benzoesaeure GK; Benzoesaeure GV; Carboxybenzene; Dracylic acid; Phenylcarboxylic acid; Phenylformic acid; Retarder BA; Retardex; Salvo, liquid; Solvo, powder; Tenn-Plas; Acide benzoique; Benzoic acid, tech.; Kyselina benzoova; Benzoesaeure; Salvo powder; E 210; HA 1; HA 1 (acid); Phenylcarboxy; Benzenemethonic acid; Diacylic acid; Flowers of benjamin; Flowers of benzoin; Oracylic acid; Retarder BAX; NSC 149
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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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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Individual Reactions
+
=
By formula: C7H5O2- + H+ = C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1423. ± 9.2 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 1423. ± 12. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder; B |
| ΔrH° | 1423. ± 9.2 | kJ/mol | G+TS | Caldwell, Renneboog, et al., 1989 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Recalculated from data in paper; error in Table vs. ladder; B |
| ΔrG° | 1394. ± 8.4 | kJ/mol | IMRE | Caldwell, Renneboog, et al., 1989 | gas phase; B |
+
= (
•
)
By formula: Br- + C7H6O2 = (Br- • C7H6O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 76.6 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 84. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 41. ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff measured at 423 K, ΔSaff taken as that of PhNO2..Br-; B |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 41. | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
+
=
+
By formula: H2O + C7H5ClO = C7H6O2 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.04 ± 0.21 | kJ/mol | Cm | Moselhy and Pritchard, 1975 | liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS |
| ΔrH° | -101.9 | kJ/mol | Cm | Carson, Pritchard, et al., 1950 | liquid phase; Heat of hydrolysis; ALS |
+
= 2
By formula: C7H6O + C7H6O3 = 2C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -316. ± 13. | kJ/mol | Cm | Briner and Chastonay, 1954 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -317. ± 13. kJ/mol; ALS |
+
=
+
By formula: C7H5BrO + H2O = HBr + C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -113.1 | kJ/mol | Cm | Carson, Pritchard, et al., 1950 | liquid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: C7H5IO + H2O = HI + C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -102.4 | kJ/mol | Cm | Carson, Pritchard, et al., 1950 | liquid phase; Heat of hydrolysis; ALS |
+
=
+
By formula: H2O + C8H8O2 = C7H6O2 + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -73.0 ± 1.9 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; 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.
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [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]
Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P.,
Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-,
J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014
. [all data]
Moselhy and Pritchard, 1975
Moselhy, G.M.; Pritchard, H.O.,
The thermochemistry of the chloro-benzoyl chlorides,
J. Chem. Thermodyn., 1975, 7, 977-982. [all data]
Carson, Pritchard, et al., 1950
Carson, A.S.; Pritchard, H.O.; Skinner, H.A.,
The heats of hydrolysis of the benzoyl halides,
J. Chem. Soc., 1950, 656-659. [all data]
Davies, Dunning, et al., 1972
Davies, J.V.; Dunning, B.K.; Pritchard, H.O.,
The enthalpy of formation of benzoyl chloride,
J. Chem. Thermodyn., 1972, 4, 731-737. [all data]
Briner and Chastonay, 1954
Briner, E.; Chastonay, P.,
Etude thermochemique de l'autoxydation de Valdehyde benzoique,
Helv. Chim. Acta, 1954, 238, 539-541. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A.,
Effect of the acyl substituent on the equilibrium constant for hydration of esters,
Can. J. Chem., 1980, 58, 1281-1294. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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