Salicylic acid

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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
Δfgas-118.5 ± 0.33kcal/molCcrSabbah and Le, 1993ALS
Δfgas-117.9kcal/molN/AColomina, Jimenez, et al., 1980Value 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
Δfgas-116.9kcal/molN/AVerkade, 1932Value 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

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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
Δfsolid-141.5 ± 0.31kcal/molCcrSabbah and Le, 1993ALS
Δfsolid-140.9 ± 0.26kcal/molCcbColomina, Jimenez, et al., 1980ALS
Δfsolid-139.9kcal/molCcbVerkade, 1932ALS
Quantity Value Units Method Reference Comment
Δcsolid-723. ± 1.kcal/molAVGN/AAverage of 12 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar41.20cal/mol*KN/ARabinovich, Sheiman, et al., 1986DH
solid,1 bar42.59cal/mol*KN/AParks and Light, 1934Extrapolation below 90 K, 57.32 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
38.46298.15Rabinovich, Sheiman, et al., 1986T = 5 to 460 K.; DH
24.90293.Campbell and Campbell, 1940DH
38.10288.6Parks and Light, 1934T = 96 to 289 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:
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
Tfus432. ± 1.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δsub22. ± 2.kcal/molAVGN/AAverage of 7 values; Individual data points

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
484.20.026Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
19.0460.AStephenson and Malanowski, 1987Based 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 529.3.568061126.012-212.625Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
22.7 ± 0.1333.CSabbah and Le, 1993AC
22.9 ± 0.2315.MEColomina, Jimenez, et al., 1980, 2Based on data from 307. to 324. K. See also Colomina, Jimenez, et al., 1981.; AC
22.7 ± 0.1322.TEDe Kruif and Van Ginkel, 1977Based on data from 312. to 332. K.; AC
22.3 ± 0.2322.MEDe Kruif and Van Ginkel, 1977Based on data from 312. to 332. K.; AC
23.7 ± 0.5313.MEArshadi, 1974Based on data from 298. to 328. K.; AC
22.7 ± 0.1368. to 408.N/AMalaspina, 1973AC
22.7 ± 0.1368. to 408.GSDavies and Jones, 1954See also Cox and Pilcher, 1970 and Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
5.8795431.8N/ARabinovich, Sheiman, et al., 1986DH
6.48434.1DSCGood and Rodriguez-Hornedo, 2009AC
5.509432.5DSCPeña, Escalera, et al., 2009AC
5.844431.1N/APinto, Diogo, et al., 2005See also Mota, Queimada, et al., 2008.; AC
5.88431.8N/ADomalski and Hearing, 1996See also Sabbah and Le, 1993.; AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
13.6431.8Rabinovich, Sheiman, et al., 1986DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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- + Hydrogen cation = Salicylic acid

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr325.5 ± 2.2kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr317.8 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Aspirin + Water = Acetic acid + Salicylic acid

By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3

Quantity Value Units Method Reference Comment
Δr-6.50 ± 0.07kcal/molCmNelander, 1964solid phase; Heat of hydrolysis; ALS

References

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

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