Salicylic acid

• Formula: C₇H₆O₃
• Molecular weight: 138.1207
• IUPAC Standard InChI: InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Copy

  
• IUPAC Standard InChIKey: YGSDEFSMJLZEOE-UHFFFAOYSA-N Copy
• 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)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Options:
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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, Mass spectrum (electron ionization), 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.

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

Constant pressure heat capacity of solid

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:
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

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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 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

 +  =  + 

By formula: C₉H₈O₄ + H₂O = C₂H₄O₂ + C₇H₆O₃

Gas phase ion energetics 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

View reactions leading to C₇H₆O₃⁺ (ion structure unspecified)

De-protonation reactions

C₇H₅O₃^- +  =

By formula: C₇H₅O₃^- + H⁺ = C₇H₆O₃

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, 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]

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, 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)
  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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