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 |
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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C7H6O3+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 ± 0.2 | EI | Benoit, 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5O+ | 14.6 ± 0.2 | CO+OH | EI | Benoit, 1973 | LLK |
C7H5O2+ | 12.0 ± 0.2 | OH | EI | Benoit, 1973 | LLK |
De-protonation 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 |
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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Due to licensing restrictions, this spectrum cannot be downloaded.
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 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1537.7 | Tret'yakov, 2008 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1558. | Jerkovic, Hegic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | HP-5 MS | 1558. | Jerkovic and Marijanovic, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | HP-5 MS | 1558. | Jerkovic, Tuberso, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1577. | Alissandrakis, Kibaris, et al., 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(3min) => 2C/min => 180C => 10C/min => 250C(5min) |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
Benoit, 1973
Benoit, F.,
Substituent effects in mass spectrometry. III. Substituent effects in the dissociation of the molecular ions of para and meta subtituted benzoic acids,
Org. Mass Spectrom., 1973, 7, 295. [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]
Tret'yakov, 2008
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2008. [all data]
Jerkovic, Hegic, et al., 2010
Jerkovic, I.; Hegic, G.; Marijanovic, Z.; Bubalo, D.,
Organic extractives from Mentha spp. honey and the bee-stomach: methyl syringate, vomifoliol, terpenediol I, hotrienol, and other compounds,
Molecules, 2010, 15, 4, 2911-2924, https://doi.org/10.3390/molecules15042911
. [all data]
Jerkovic and Marijanovic, 2010
Jerkovic, I.; Marijanovic, Z.,
Oak (Quercus frainetto Ten.) honeydaw honey - approach to screening of volatile organic composition and antioxidant capacity (DPPH and FRAP assay),
Molecules, 2010, 15, 5, 3744-3756, https://doi.org/10.3390/molecules15053744
. [all data]
Jerkovic, Tuberso, et al., 2010
Jerkovic, I.; Tuberso, C.I.G.; Gugic, M.; Bubalo, D.,
Composition of Sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds,
Molecules, 2010, 15, 9, 6375-6385, https://doi.org/10.3390/molecules15096375
. [all data]
Alissandrakis, Kibaris, et al., 2005
Alissandrakis, E.; Kibaris, A.C.; Tarantilis, P.A.; Harizanis, P.C.; Polissiou, M.,
Flavour compounds of Greek cotton honey,
J. Sci. Food Agric., 2005, 85, 9, 1444-1452, https://doi.org/10.1002/jsfa.2124
. [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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy 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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