Benzoic acid, 4-hydroxy-

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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-492.6 ± 2.2kJ/molCcrSabbah and Le, 1993ALS
Δfgas-480.5kJ/molN/AColomina, Jimenez, et al., 1980Value 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
Δfsolid-606.6 ± 2.1kJ/molCcrSabbah and Le, 1993ALS
Δfsolid-594.5 ± 1.0kJ/molCcbColomina, Jimenez, et al., 1980ALS
Quantity Value Units Method Reference Comment
Δcsolid-3005.4 ± 2.1kJ/molCcrSabbah and Le, 1993Corresponding Δfsolid = -606.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-3017.6 ± 0.5kJ/molCcbColomina, Jimenez, et al., 1980Corresponding Δfsolid = -594.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar175.7J/mol*KN/AParks and Light, 1934Extrapolation below 90 K, 55.35 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
155.2283.8Parks and Light, 1934T = 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
Tfus488.1KN/AArmstrong, James, et al., 1979Uncertainty assigned by TRC = 0.5 K; TRC
Tfus489.KN/AHerbert, 1967Uncertainty assigned by TRC = 1. K; TRC
Tfus489.35KN/ADavies and Jones, 1954Uncertainty assigned by TRC = 0.7 K; TRC
Tfus486.KN/AKing, McWhirter, et al., 1945Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Δsub117.0 ± 0.5kJ/molCPinto, Diogo, et al., 2005AC
Δsub114.05 ± 0.69kJ/molCSabbah and Le, 1993ALS
Δsub114.0kJ/molN/ASabbah and Le, 1993DRB
Δsub114.1 ± 0.7kJ/molN/ASabbah and Le, 1993AC
Δsub116.1 ± 0.4kJ/molVDavies and Jones, 1954ALS

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
112.4 ± 0.7363.CSabbah and Le, 1993AC
116.3398. to 433.GSDavies and Jones, 1954See also Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
30.9488.1N/AARMSTRONG, JAMES, et al., 2011AC
30.85489.N/ANordström and Rasmuson, 2006AC
31.4487.2N/AGracin and Rasmuson, 2002AC
32.0488.DSCHeath, Singh, et al., 1992AC

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 = Benzoic acid, 4-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr1405. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.; B
Quantity Value Units Method Reference Comment
Δr1376. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.; B

Benzoic acid, 4-(acetyloxy)- + Water = Acetic acid + Benzoic acid, 4-hydroxy-

By formula: C9H8O4 + H2O = C2H4O2 + C7H6O3

Quantity Value Units Method Reference Comment
Δr-20.6 ± 0.3kJ/molCmNelander, 1964solid 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 ± 0.2EIBenoit, 1973LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5O+14.6 ± 0.2CO+OHEIBenoit, 1973LLK
C7H5O2+12.0 ± 0.2OHEIBenoit, 1973LLK

De-protonation reactions

C7H5O3- + Hydrogen cation = Benzoic acid, 4-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Δr1405. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.; B
Quantity Value Units Method Reference Comment
Δr1376. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas 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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Mass 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

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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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UVVis 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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1537.7Tret'yakov, 200830. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS1558.Jerkovic, Hegic, et al., 201030. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min
CapillaryHP-5 MS1558.Jerkovic and Marijanovic, 201030. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min
CapillaryHP-5 MS1558.Jerkovic, Tuberso, et al., 201030. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5MS1577.Alissandrakis, Kibaris, et al., 200530. 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