Benzoic acid, 2-amino-
- Formula: C7H7NO2
- Molecular weight: 137.1360
- IUPAC Standard InChI: InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
- IUPAC Standard InChIKey: RWZYAGGXGHYGMB-UHFFFAOYSA-N
- CAS Registry Number: 118-92-3
- 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: Anthranilic acid; o-Aminobenzoic acid; o-Carboxyaniline; 2-Aminobenzoic acid; 2-Carboxyaniline; NCI-C01730; 1-Amino-2-carboxybenzene; o-Anthranilic acid; Benzoic acid, o-amino-; Kyselina o-aminobenzoova; Kyselina anthranilova; ortho-Aminobenzoic acid; Vitamin L1; NSC 144
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -296.2 ± 1.6 | kJ/mol | Ccr | Nabavian, Sabbah, et al., 1977 | Author was aware that data differs from previously reported values |
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 | -401.1 ± 1.2 | kJ/mol | Ccr | Nabavian, Sabbah, et al., 1977 | Author was aware that data differs from previously reported values; ALS |
| ΔfH°solid | -401. ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=4.9±0.1, see Lebedeva, Rjadnenko, et al., 1969; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3353.83 ± 0.80 | kJ/mol | Ccr | Nabavian, Sabbah, et al., 1977 | Author was aware that data differs from previously reported values; ALS |
| ΔcH°solid | -3354. ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=4.9±0.1, see Lebedeva, Rjadnenko, et al., 1969; ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 187.0 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100 C. Mean value.; DH |
| 165.3 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 160 C.; 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 417.8 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.5 K; with possible decomposition; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 104.9 ± 1.0 | kJ/mol | V | Nabavian, Sabbah, et al., 1977 | Author was aware that data differs from previously reported values; ALS |
| ΔsubH° | 104.9 ± 1.0 | kJ/mol | V | Sabbah, Chastelet, et al., 1974 | ALS |
| ΔsubH° | 111.6 ± 1.7 | kJ/mol | N/A | Arnold and Jones, 1972 | AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 20.5 | 417.8 | Acree, 1991 | AC |
| 20.380 | 417.8 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 48.8 | 417.8 | Andrews, Lynn, et al., 1926 | DH |
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 by: John E. Bartmess
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
C7H6NO2- + =
By formula: C7H6NO2- + H+ = C7H7NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1411. ± 9.2 | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1382. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase |
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 | 1413.1 | Tret'yakov, 2007 | 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 | 1416. | 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 |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2997. | Parada and Duque, 1998 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
| Capillary | DB-Wax | 3021. | Parada and Duque, 1998 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nabavian, Sabbah, et al., 1977
Nabavian, P.M.; Sabbah, R.; Chastel, R.; Laffitte, M.,
Thermodynamique de composes azotes. II. Etude thermochimique des acides aminobenzoiques, de la pyrimidine, de l'uracile et de la thymine.,
J. Chim. Phys., 1977, 74, 115-126. [all data]
Lebedeva, Gutner, et al., 1971
Lebedeva, N.D.; Gutner, N.M.; Ryadnenko, V.L.,
Heats of combustion and formation of certain aromatic amino-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 561-562. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (2), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 231-237. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J.,
The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds,
J. Am. Chem. Soc., 1926, 48, 1274. [all data]
Sabbah, Chastelet, et al., 1974
Sabbah, R.; Chastelet, R.; Laffitte, M.,
Thermodynamic de composès azotes. I. Etude calorimètrique des enthalpies de sublimation des trios acides aminobenzoïques,
Can. J. Chem., 1974, 52, 2201. [all data]
Arnold and Jones, 1972
Arnold, P.R.; Jones, F.,
Polymorphism in Anthranilic Acid Crystals---Examination by DTA and DSC,
Molecular Crystals and Liquid Crystals, 1972, 19, 2, 133-140, https://doi.org/10.1080/15421407208083859
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [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]
Parada and Duque, 1998
Parada, F.; Duque, C.,
Studies on the aroma of piñuela fruit pulp (Bromelia plumieri): Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors,
J. Hi. Res. Chromatogr., 1998, 21, 10, 577-581, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<577::AID-JHRC577>3.0.CO;2-V
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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 ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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