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)
- Download the identifier in a file.
- 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
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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
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | -469.1 ± 1.3 | kJ/mol | Ccr | Sabbah and Le, 1993 | ALS |
![]() | -465.5 | kJ/mol | N/A | Colomina, Jimenez, et al., 1980 | Value computed using «DELTA»fHsolid° value of -590.5±1.0 kj/mol from Colomina, Jimenez, et al., 1980 and «DELTA»subH° 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 |
---|---|---|---|---|---|
![]() | -594.1 ± 1.1 | kJ/mol | Ccr | Sabbah and Le, 1993 | ALS |
![]() | -590.5 ± 1.0 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1980 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
![]() | -3017.9 ± 1.1 | kJ/mol | Ccr | Sabbah and Le, 1993 | Corresponding «DELTA»fHºsolid = -594.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
![]() | -3021.6 ± 0.4 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1980 | Corresponding «DELTA»fHºsolid = -590.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 177.0 | J/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 (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
157.3 | 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, Kenneth Kroenlein 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 |
![]() | 118.3 ± 1.1 | kJ/mol | C | Pinto, Diogo, et al., 2005 | AC |
![]() | 124.99 ± 0.74 | kJ/mol | C | Sabbah and Le, 1993 | ALS |
![]() | 125.0 | kJ/mol | N/A | Sabbah and Le, 1993 | DRB |
![]() | 125.0 ± 0.74 | kJ/mol | N/A | Sabbah and Le, 1993 | AC |
Enthalpy of sublimation
![]() |
Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
123.5 ± 0.74 | 363. | C | Sabbah and Le, 1993 | AC |
Enthalpy of fusion
![]() |
Temperature (K) | Reference | Comment |
---|---|---|---|
36.5 | 476.4 | Pinto, Diogo, et al., 2005 | AC |
26.2 | 475.1 | Domalski and Hearing, 1996 | See also Sabbah and Le, 1993.; 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 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
C7H5O3- + =
By formula: C7H5O3- + H+ = C7H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 1417. ± 8.8 | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 1387. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
NIST MS number | 365468 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]
Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B.,
Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria,
J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 cH°solid
Enthalpy of combustion of solid at standard conditions fH°gas
Enthalpy of formation of gas at standard conditions fH°solid
Enthalpy of formation of solid at standard conditions fusH
Enthalpy of fusion rG°
Free energy of reaction at standard conditions rH°
Enthalpy of reaction at standard conditions subH
Enthalpy of sublimation subH°
Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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