Benzoic acid, 4-hydroxy-
- Formula: C7H6O3
- Molecular weight: 138.1207
- IUPAC Standard InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N
- CAS Registry Number: 99-96-7
- 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, p-hydroxy-; p-Hydroxybenzoic acid; p-Salicylic acid; Paraben-acid; 4-Carboxyphenol; 4-Hydroxybenzoic acid; para-Hydroxybenzoic acid; Hydroxybenzoic acid, para; Kyselina 4-hydroxybenzoova; NSC 4961; Paraben
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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 |
---|---|---|---|---|---|
ΔfH°gas | -117.7 ± 0.53 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
ΔfH°gas | -114.8 | kcal/mol | N/A | Colomina, Jimenez, et al., 1980 | Value computed using ΔfHsolid° value of -594.5±1.0 kj/mol from Colomina, Jimenez, et al., 1980 and ΔsubH° value of 114.0 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 | -145.0 ± 0.50 | kcal/mol | Ccr | Sabbah and Le, 1993 | ALS |
ΔfH°solid | -142.1 ± 0.24 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1980 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -718.31 ± 0.50 | kcal/mol | Ccr | Sabbah and Le, 1993 | Corresponding ΔfHºsolid = -145.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -721.2 ± 0.1 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1980 | Corresponding ΔfHºsolid = -142.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 41.99 | cal/mol*K | N/A | Parks and Light, 1934 | Extrapolation below 90 K, 55.35 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.09 | 283.8 | Parks and Light, 1934 | T = 95 to 284 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 | 488.1 | K | N/A | Armstrong, James, et al., 1979 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 489. | K | N/A | Herbert, 1967 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 489.35 | K | N/A | Davies and Jones, 1954 | Uncertainty assigned by TRC = 0.7 K; TRC |
Tfus | 486. | K | N/A | King, McWhirter, et al., 1945 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 28.0 ± 0.1 | kcal/mol | C | Pinto, Diogo, et al., 2005 | AC |
ΔsubH° | 27.26 ± 0.16 | kcal/mol | C | Sabbah and Le, 1993 | ALS |
ΔsubH° | 27.25 | kcal/mol | N/A | Sabbah and Le, 1993 | DRB |
ΔsubH° | 27.3 ± 0.2 | kcal/mol | N/A | Sabbah and Le, 1993 | AC |
ΔsubH° | 27.7 ± 0.1 | kcal/mol | V | Davies and Jones, 1954 | ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.9 ± 0.2 | 363. | C | Sabbah and Le, 1993 | AC |
27.80 | 398. to 433. | GS | Davies and Jones, 1954 | See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.39 | 488.1 | N/A | ARMSTRONG, JAMES, et al., 2011 | AC |
7.373 | 489. | N/A | Nordström and Rasmuson, 2006 | AC |
7.50 | 487.2 | N/A | Gracin and Rasmuson, 2002 | AC |
7.65 | 488. | DSC | Heath, Singh, et al., 1992 | 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 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° | 335.9 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; This is probably the phenolic site acidity, not the carboxylic.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 328.9 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; This is probably the phenolic site acidity, not the carboxylic.; B |
By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.93 ± 0.08 | kcal/mol | Cm | Nelander, 1964 | solid phase; Heat of hydrolysis; ALS |
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 | 352453 |
UV/Visible spectrum
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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Grammaticakis, 1953 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 3324 |
Instrument | n.i.g. |
Melting point | 214.5 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
Armstrong, James, et al., 1979
Armstrong, N.A.; James, K.C.; Wong, C.K.,
Inter-relationships between solubilities, distribution coefficients and melting points of some substituted benzoic and phenylacetic acids,
J. Pharm. Pharmacol., 1979, 31, 1, 627, https://doi.org/10.1111/j.2042-7158.1979.tb13606.x
. [all data]
Herbert, 1967
Herbert, A.J.,
Transition temperatures and transition energies of the p-n-alkoxy benzoic acids, from n-propyl to n-octadecyl,
Trans. Faraday Soc., 1967, 63, 555, https://doi.org/10.1039/tf9676300555
. [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]
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]
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]
ARMSTRONG, JAMES, et al., 2011
ARMSTRONG, N.A.; JAMES, K.C.; WONG, C.K.,
Inter-relationships between solubilities, distribution coefficients and melting points of some substituted benzoic and phenylacetic acids,
Journal of Pharmacy and Pharmacology, 2011, 31, 1, 627-631, https://doi.org/10.1111/j.2042-7158.1979.tb13606.x
. [all data]
Nordström and Rasmuson, 2006
Nordström, Fredrik L.; Rasmuson, Åke C.,
Phase equilibria and thermodynamics ofp-hydroxybenzoic acid,
J. Pharm. Sci., 2006, 95, 4, 748-760, https://doi.org/10.1002/jps.20569
. [all data]
Gracin and Rasmuson, 2002
Gracin, Sandra; Rasmuson, Åke C.,
Solubility of Phenylacetic Acid, p -Hydroxyphenylacetic Acid, p -Aminophenylacetic Acid, p -Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents,
J. Chem. Eng. Data, 2002, 47, 6, 1379-1383, https://doi.org/10.1021/je0255170
. [all data]
Heath, Singh, et al., 1992
Heath, E.A.; Singh, P.; Ebisuzaki, Y.,
Structure of p-hydroxybenzoic acid and p-hydroxybenzoic acid-acetone complex (2/1),
Acta Crystallogr Sect C Cryst Struct Commun, 1992, 48, 11, 1960-1965, https://doi.org/10.1107/S0108270192002361
. [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]
Grammaticakis, 1953
Grammaticakis, P.,
Contribution a l'etude de l'absorption dans l'U.-V. moyen et le visible de quelques aldehydes et cetones aromatiques ainsi que de certains de leurs derives fonctionnels, (Premier memoire),
Bull. Soc. Chim. Fr., 1953, 20, 821-826. [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), UV/Visible spectrum, 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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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