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)
- 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 |
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 |
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
| 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, 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.
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]
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, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔfH°gas Enthalpy of formation of gas at standard conditions 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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