Isophthalic acid
- Formula: C8H6O4
- Molecular weight: 166.1308
- IUPAC Standard InChI: InChI=1S/C8H6O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
- IUPAC Standard InChIKey: QQVIHTHCMHWDBS-UHFFFAOYSA-N
- CAS Registry Number: 121-91-5
- 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: 1,3-Benzenedicarboxylic acid; m-Benzenedicarboxylic acid; m-Phthalic acid; Benzene,1,3-dicarboxylic acid; Acide isophtalique; Kyselina isoftalova; IPA; m-Dicarboxybenzene; NSC 15310
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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 | -801.5 ± 1.5 | kJ/mol | Ccb | Karyakin, Rabinovich, et al., 1978 | see Karyakin, Rabinovich, et al., 1975 and Karyakin, Kamelova, et al., 1973; ALS |
| ΔfH°solid | -803.04 | kJ/mol | Ccb | Schwabe and Wagner, 1961 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3204.1 ± 1.5 | kJ/mol | Ccb | Karyakin, Rabinovich, et al., 1978 | see Karyakin, Rabinovich, et al., 1975 and Karyakin, Kamelova, et al., 1973; Corresponding ΔfHºsolid = -801.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3202.6 ± 0.50 | kJ/mol | Ccb | Schwabe and Wagner, 1961 | Corresponding ΔfHºsolid = -802.95 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3217.85 | kJ/mol | Ccb | Verkade, Coops, et al., 1928 | Corresponding ΔfHºsolid = -787.72 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3215.37 | kJ/mol | Ccb | Verkade, 1926 | Corresponding ΔfHºsolid = -790.20 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 201.7 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100 C. Mean value.; DH |
| 201.7 | 323. | Satoh and Sogabe, 1939 | T = 0 to 100 C. Mean value.; 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 by: William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 142.0 ± 0.7 | kJ/mol | C | Sabbah and Perez, 1999 |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 134.6 ± 1.6 | 450. | ME | Kozyro, Maksimuk, et al., 2000 | Based on data from 424. to 476. K. |
| 114.2 | 508. | A | Stephenson and Malanowski, 1987 | Based on data from 493. to 563. K. See also Kraus, Beranek, et al., 1962. |
| 106.7 ± 2.2 | 523. | GS | Kraus, Beranek, et al., 1962 | Based on data from 493. to 563. K. See also Cox and Pilcher, 1970. |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference |
|---|---|---|---|
| 43.2 | 617.4 | DTA | Sabbah and Perez, 1999 |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 10. ± 0.2 | EI | Benoit, 1973 |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7H5O2+ | 12.4 ± 0.2 | COOH | EI | Benoit, 1973 | |
| C8H5O3+ | 12.2 ± 0.2 | OH | EI | Benoit, 1973 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Sokolov, L.B.,
Thermodynamics of the synthesis of isomeric poly(phenylenephthalamides),
Vysokomol. Soedin. Ser. B, 1978, 20, 662-666. [all data]
Karyakin, Rabinovich, et al., 1975
Karyakin, N.V.; Rabinovich, I.B.; Kamelova, G.P.; Mochalov, A.N.; Tseitlin, G.M.; Kulagin, V.N.; Korshak, V.V.,
Thermodynamics of the synthesis of poly-2,2'-(m-phenylene)-5-5'-dibenzoxazolomethane,
Polym. Sci. USSR, 1975, 17, 1127-1133. [all data]
Karyakin, Kamelova, et al., 1973
Karyakin, N.V.; Kamelova, G.P.; Yurchenko, V.N.; Kiparisova, e.G.; Korshak, V.V.; Tseitlin, G.M.; Kulagin, V.N.; Rabinovich, I.B.,
Thermodynamics of the synthesis of poly[2,2'-(m-phenylene)-5,5'-dibenzoxazolemethane] from 3,3'-diamino-4,4'-dihydroxydiphenylmethane and isophthalic acid,
Tr. Khim. Khim. Tekhnol., 1973, 71-72. [all data]
Schwabe and Wagner, 1961
Schwabe, K.; Wagner, W.,
Verbrennungs- und bildungswarmen der drei isomeren phthalsauren,
Z. Electrochem., 1961, 65, 812-815. [all data]
Verkade, Coops, et al., 1928
Verkade, P.E.; Coops, J., Jr.; Maan, Chr.J.,
Calorimetrische Untersuchungen. XV. Thermochemische studien uber cycloparaffine und ihre derivate: 1. Experimentelle daten fur funf- und sechsgliedrige cyclische diole,
Ann., 1928, 467, 217-239. [all data]
Verkade, 1926
Verkade, P.E.,
Verbrandingswarmten van plaatsings-isomere benzol-derivaten en de theorie der geinduceerde alterneeren de polatiteit,
Verslag Akad. Wetenschappen Amsterdam, 1926, 35, 492-504. [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. (4), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 246-251. [all data]
Satoh and Sogabe, 1939
Satoh, S.; Sogabe, T.,
The specific heats of some solid aromatic acids and their ammonium salts and the atomic heat of nitrogen,
Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, 36, 449-457. [all data]
Sabbah and Perez, 1999
Sabbah, Raphaël; Perez, Laurence,
Étude thermodynamique des acides phtalique, isophtalique et téréphtalique,
Revue canadienne de chimie, 1999, 77, 9, 1508-1513, https://doi.org/10.1139/cjc-77-9-1508
. [all data]
Kozyro, Maksimuk, et al., 2000
Kozyro, A.A.; Maksimuk, Yu.V.; Kabo, G.Ya.,
Thermodynamics of vaporization of phthalic acids and additivity of enthalpies and entropies of sublimation of benzocarboxylic acids,
Zh. Prikl. Khim. (S.-Peterburg), 2000, 73, 2, 199. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Kraus, Beranek, et al., 1962
Kraus, M.; Beranek, L.; Kochloeff, K.; Bazant, V.,
Chem. Prum., 1962, 12, 649. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion 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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