Salicylic acid
- Formula: C7H6O3
- Molecular weight: 138.1207
- IUPAC Standard InChIKey: YGSDEFSMJLZEOE-UHFFFAOYSA-N
- CAS Registry Number: 69-72-7
- 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, 2-hydroxy-; o-Hydroxybenzoic acid; Phenol-2-carboxylic acid; Psoriacid-S-Stift; Retarder W; Rutranex; Salicylic acid collodion; Salonil; 2-Hydroxybenzoic acid; Acido salicilico; Keralyt; Kyselina 2-hydroxybenzoova; Kyselina salicylova; Orthohydroxybenzoic acid; Duoplant; Freezone; Ionil; Saligel; Compound W; 2-Hydroxybenzenecarboxylic acid; 2-Carboxyphenol; o-Carboxyphenol; Advanced pain relief callus removers; Advanced pain relief corn removers; Clear away wart remover; Dr. Scholl's Callus Removers; Dr. Scholl's Corn Removers; Dr. Scholl's Wart Remover Kit; Duofil Wart Remover; Ionil plus; Salicylic acid soap; Stri-Dex; Benzoic acid, o-hydroxy-; NSC 180; Trans-Ver-Sal; Domerine; Duofilm; Fostex; Pernox; Salicylic acid & Sulfur Soap; Sebucare; Sebulex; component of Fostex medicated bar and cream; component of Keralyt; Retarder SAX; component of Solarcaine first aid spray; component of Tinver; 7681-06-3; 8052-31-1; Salicyclic acid; Domerine (Salt/Mix); Duofilm (Salt/Mix); Fostex (Salt/Mix); Pernox (Salt/Mix); Salicylic acid & Sulfur Soap (Salt/Mix); Sebucare (Salt/Mix); Sebulex (Salt/Mix); component of Fostex medicated bar and cream (Salt/Mix); component of Keralyt (Salt/Mix); Retarder SAX (Salt/Mix); component of Solarcaine first aid spray (Salt/Mix); component of Tinver (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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 | -118.5 ± 0.33 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
ΔfH°gas | -117.9 | kcal/mol | N/A | Colomina, Jimenez, et al., 1980 | Value computed using ΔfHsolid° value of -589.7±1.1 kj/mol from Colomina, Jimenez, et al., 1980 and ΔsubH° value of 96.3 kj/mol from Colomina, Jimenez, et al., 1980.; DRB |
ΔfH°gas | -116.9 | kcal/mol | N/A | Verkade, 1932 | Value computed using ΔfHsolid° value of -585.3 kj/mol from Verkade, 1932 and ΔsubH° value of 96.3 kj/mol from Verkade, 1932.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -141.5 ± 0.31 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
ΔfH°solid | -140.9 ± 0.26 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1980 | ALS |
ΔfH°solid | -139.9 | kcal/mol | Ccb | Verkade, 1932 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -723. ± 1. | kcal/mol | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 41.20 | cal/mol*K | N/A | Rabinovich, Sheiman, et al., 1986 | DH |
S°solid,1 bar | 42.59 | cal/mol*K | N/A | Parks and Light, 1934 | Extrapolation below 90 K, 57.32 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.46 | 298.15 | Rabinovich, Sheiman, et al., 1986 | T = 5 to 460 K.; DH |
24.90 | 293. | Campbell and Campbell, 1940 | DH |
38.10 | 288.6 | Parks and Light, 1934 | T = 96 to 289 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
BS - Robert L. Brown and Stephen E. Stein
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.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 432. ± 1. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22. ± 2. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
484.2 | 0.026 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.0 | 460. | A | Stephenson and Malanowski, 1987 | Based on data from 445. to 504. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
386.8 to 529. | 3.56806 | 1126.012 | -212.625 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.7 ± 0.1 | 333. | C | Sabbah and Le, 1993 | AC |
22.9 ± 0.2 | 315. | ME | Colomina, Jimenez, et al., 1980, 2 | Based on data from 307. to 324. K. See also Colomina, Jimenez, et al., 1981.; AC |
22.7 ± 0.1 | 322. | TE | De Kruif and Van Ginkel, 1977 | Based on data from 312. to 332. K.; AC |
22.3 ± 0.2 | 322. | ME | De Kruif and Van Ginkel, 1977 | Based on data from 312. to 332. K.; AC |
23.7 ± 0.5 | 313. | ME | Arshadi, 1974 | Based on data from 298. to 328. K.; AC |
22.7 ± 0.1 | 368. to 408. | N/A | Malaspina, 1973 | AC |
22.7 ± 0.1 | 368. to 408. | GS | Davies and Jones, 1954 | See also Cox and Pilcher, 1970 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.8795 | 431.8 | N/A | Rabinovich, Sheiman, et al., 1986 | DH |
6.48 | 434.1 | DSC | Good and Rodriguez-Hornedo, 2009 | AC |
5.509 | 432.5 | DSC | Peña, Escalera, et al., 2009 | AC |
5.844 | 431.1 | N/A | Pinto, Diogo, et al., 2005 | See also Mota, Queimada, et al., 2008.; AC |
5.88 | 431.8 | N/A | Domalski and Hearing, 1996 | See also Sabbah and Le, 1993.; AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.6 | 431.8 | Rabinovich, Sheiman, et al., 1986 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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 |
---|---|---|---|---|---|
ΔrH° | 325.5 ± 2.2 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 317.8 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -6.50 ± 0.07 | kcal/mol | Cm | Nelander, 1964 | solid phase; Heat of hydrolysis; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References, Notes
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
View reactions leading to C7H6O3+ (ion structure unspecified)
De-protonation reactions
C7H5O3- + =
By formula: C7H5O3- + H+ = C7H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 325.5 ± 2.2 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 317.8 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
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]
Verkade, 1932
Verkade, P.-E.,
L'acide salicylique comme substance-etalon secondaire de calorimetrie,
J. Chim. Phys., 1932, 29, 297-301. [all data]
Rabinovich, Sheiman, et al., 1986
Rabinovich, I.B.; Sheiman, M.S.; Kamelova, G.P.; Nistratov, V.P.,
Heat capacity and thermodynamic functions of salicylic acid, 1986, Termodinam. [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]
Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R.,
The heats of solution, heats of formation,
specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Colomina, Jimenez, et al., 1980, 2
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of o-, m-, and p-hydroxybenzoic acids,
J. Therm Anal. Calorim., 1980, 11, 3-19-1/3-19-6. [all data]
Colomina, Jimenez, et al., 1981
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Propiedades Termoquimicas de derivados del acido benzoico. IX. Entalpias de combustion y formacion de los acidos o-, m-, y p-hidroxibenzoicos,
An. Quim., 1981, 77, 114. [all data]
De Kruif and Van Ginkel, 1977
De Kruif, C.G.; Van Ginkel, C.H.D.,
Torsion-weighing effusion vapour-pressure measurements on organic compounds,
The Journal of Chemical Thermodynamics, 1977, 9, 8, 725-730, https://doi.org/10.1016/0021-9614(77)90015-5
. [all data]
Arshadi, 1974
Arshadi, Mohammed R.,
Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method,
J. Chem. Soc., Faraday Trans. 1, 1974, 70, 0, 1569, https://doi.org/10.1039/f19747001569
. [all data]
Malaspina, 1973
Malaspina, L.,
Microcalorimetric determination of the enthalpy of sublimation of benzoic acid and anthracene,
J. Chem. Phys., 1973, 59, 1, 387, https://doi.org/10.1063/1.1679817
. [all data]
Davies and Jones, 1954
Davies, M.; Jones, J.I.,
The sublimation pressures and heats of sublimation of some carboxylic acids,
Trans. Faraday Soc., 1954, 50, 1042. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Good and Rodriguez-Hornedo, 2009
Good, David J.; Rodriguez-Hornedo, Nair,
Solubility Advantage of Pharmaceutical Cocrystals,
Crystal Growth & Design, 2009, 9, 5, 2252-2264, https://doi.org/10.1021/cg801039j
. [all data]
Peña, Escalera, et al., 2009
Peña, M.A.; Escalera, B.; Reíllo, A.; Sánchez, A.B.; Bustamante, P.,
Thermodynamics of cosolvent action: Phenacetin, salicylic acid and probenecid,
J. Pharm. Sci., 2009, 98, 3, 1129-1135, https://doi.org/10.1002/jps.21497
. [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]
Mota, Queimada, et al., 2008
Mota, Fatima L.; Queimada, Antonio J.; Pinho, Simao P.; Macedo, Eugenia A.,
Aqueous Solubility of Some Natural Phenolic Compounds,
Ind. Eng. Chem. Res., 2008, 47, 15, 5182-5189, https://doi.org/10.1021/ie071452o
. [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]
Nelander, 1964
Nelander, L.,
The heats of hydrolysis of aspirin, thioaspirin, and their p-analogues,
Acta Chem. Scand., 1964, 18, 973-984. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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) Tboil Boiling point 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 ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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