Benzoic acid, 4-hydroxy-

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

  
• IUPAC Standard InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 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

Appearance energy determinations

De-protonation reactions

C₇H₅O₃^- +  =

By formula: C₇H₅O₃^- + H⁺ = C₇H₆O₃

Gas Chromatography

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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

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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