Benzoic acid, 3-hydroxy-
- Formula: C7H6O3
- Molecular weight: 138.1207
- IUPAC Standard InChI: InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
- IUPAC Standard InChIKey: IJFXRHURBJZNAO-UHFFFAOYSA-N
- CAS Registry Number: 99-06-9
- 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: Benzoic acid, m-hydroxy-; m-Hydroxybenzoic acid; m-Salicylic acid; 3-Carboxyphenol; 3-Hydroxybenzoic acid; meta-Hydroxybenzoic acid; Acido m-idrossibenzoico; m-Hba; Kyselina 3-hydroxybenzoova; NSC 55746
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -112.1 ± 0.31 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
| ΔfH°gas | -111.3 | kcal/mol | N/A | Colomina, Jimenez, et al., 1980 | Value computed using ΔfHsolid° value of -590.5±1.0 kj/mol from Colomina, Jimenez, et al., 1980 and ΔsubH° value of 125.0 kj/mol from Sabbah and Le, 1993.; DRB |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -142.0 ± 0.26 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
| ΔfH°solid | -141.1 ± 0.24 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1980 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -721.30 ± 0.26 | kcal/mol | Ccr | Sabbah and Le, 1993 | Corresponding ΔfHºsolid = -142.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -722.18 ± 0.1 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1980 | Corresponding ΔfHºsolid = -141.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 42.30 | cal/mol*K | N/A | Parks and Light, 1934 | Extrapolation below 90 K, 56.48 J/mol*K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 37.60 | 288.4 | Parks and Light, 1934 | T = 94 to 288 K. Value is unsmoothed experimental datum.; DH |
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 472. | K | N/A | Mayer, Howell, et al., 1990 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 364. | K | N/A | Kuhn and Dury, 1951 | Uncertainty assigned by TRC = 3. K; TRC |
| Tfus | 472. | K | N/A | King, McWhirter, et al., 1945 | Uncertainty assigned by TRC = 6. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 28.27 ± 0.26 | kcal/mol | C | Pinto, Diogo, et al., 2005 | AC |
| ΔsubH° | 29.87 ± 0.18 | kcal/mol | C | Sabbah and Le, 1993 | ALS |
| ΔsubH° | 29.88 | kcal/mol | N/A | Sabbah and Le, 1993 | DRB |
| ΔsubH° | 29.88 ± 0.18 | kcal/mol | N/A | Sabbah and Le, 1993 | AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 29.52 ± 0.18 | 363. | C | Sabbah and Le, 1993 | AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.72 | 476.4 | Pinto, Diogo, et al., 2005 | AC |
| 6.26 | 475.1 | Domalski and Hearing, 1996 | See also Sabbah and Le, 1993.; AC |
Gas Chromatography
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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
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Apieson L | 140. | 1417. | Hedin, Minyard, et al., 1967 | Nitrogen, Chromosorb W HMDS (60-80 mesh); Column length: 1.8 m |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah and Le, 1993
Sabbah, R.; Le, T.H.D.,
Etude thermodynamique des trois isomeres de l'acide bydroxybenzolque,
Can. J. Chem., 1993, 71, 1378-1383. [all data]
Colomina, Jimenez, et al., 1980
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of o-, m- and p-hydroxybenzoic acids,
J. Calorim. Anal. Therm., 1980, 11, 1-6. [all data]
Parks and Light, 1934
Parks, G.S.; Light, D.W.,
Thermal data on organic compounds. XIII. The heat capacities and entropies of n-tetradecane and the hydroxybenzoic acids. The relative free energies of some benzenoid position isomers,
J. Am. Chem. Soc., 1934, 56, 1511-1513. [all data]
Mayer, Howell, et al., 1990
Mayer, M.M.; Howell, W.J.; Tomasko, D.L.; Eckert, C.A.,
Solid-solid Equilibria in the Systems Thianthrene + Phenanthrene, Salicylic Acid + Phenanthrene, and 3-Hydroxybenzoic Acid + Phenanthrene,
J. Chem. Eng. Data, 1990, 35, 446. [all data]
Kuhn and Dury, 1951
Kuhn, R.; Dury, K.,
6-Acetylsalicylic acid,
Chem. Ber., 1951, 84, 848-50. [all data]
King, McWhirter, et al., 1945
King, L.C.; McWhirter, M.; Barton, D.M.,
Reactions of Acetophenols with Iodine and Pyridine and the Preparation of Hydroxybenzoic Acids,
J. Am. Chem. Soc., 1945, 67, 2089-92. [all data]
Pinto, Diogo, et al., 2005
Pinto, Susana S.; Diogo, Hermínio P.; Guedes, Rita C.; Costa Cabral, Benedito J.; Minas da Piedade, Manuel E.; Martinho Simões, José A.,
Energetics of Hydroxybenzoic Acids and of the Corresponding Carboxyphenoxyl Radicals. Intramolecular Hydrogen Bonding in 2-Hydroxybenzoic Acid,
J. Phys. Chem. A, 2005, 109, 42, 9700-9708, https://doi.org/10.1021/jp054220g
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Hedin, Minyard, et al., 1967
Hedin, P.A.; Minyard, J.P.; Thompson, A.C.,
Chromatographic and spectral analysis of phenolic acids and related compounds,
J. Chromatogr., 1967, 30, 43-53, https://doi.org/10.1016/S0021-9673(00)84111-4
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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