Benzoic acid, 4-methoxy-
- Formula: C8H8O3
- Molecular weight: 152.1473
- IUPAC Standard InChIKey: ZEYHEAKUIGZSGI-UHFFFAOYSA-N
- CAS Registry Number: 100-09-4
- 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: p-Anisic acid; p-Methoxybenzoic acid; Draconic acid; 4-Anisic acid; 4-Methoxybenzoic acid; Anisic acid, para; Kyselina 4-methoxybenzoova
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -451.9 ± 1.4 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 413. | J/mol*K | N/A | Alcolea P.M., 1994 | This value was calculated by semiempirical AM1 method for anti conformer. The same authors have calculated the value of S(298.15 K)=395 J/mol*K by ab initio 4-21G* basis set method. The value of 436 J/mol*K was estimated for equilibrium mixture of conformers by difference method [ Dorofeeva O.V., 1997].; GT |
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 | -561.7 ± 1.3 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3729.71 ± 0.75 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1978 | Corresponding ΔfHºsolid = -561.69 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 |
---|---|---|---|
205.0 | 323. | Satoh and Sogabe, 1941 | 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
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 |
---|---|---|---|---|---|
Tfus | 456.15 | K | N/A | Anonymous, 1988 | Uncertainty assigned by TRC = 1. K; nominal value, from the catalog; TRC |
Tfus | 456.75 | K | N/A | Marsh, 1987 | Uncertainty assigned by TRC = 0.2 K; recommended as fixed point for thermometry; TRC |
Tfus | 457.8 | K | N/A | Armstrong, James, et al., 1979 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 457. | K | N/A | Herbert, 1967 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 92. | kJ/mol | Sub-Fus | Perlovich, Volkova, et al., 2008 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 111.6 ± 0.6 | kJ/mol | GS | Perlovich, Volkova, et al., 2008 | Based on data from 316. to 369. K.; AC |
ΔsubH° | 109.8 ± 0.6 | kJ/mol | ME | Stephenson and Malanowski, 1987 | See also Colomina, Jimenez, et al., 1978.; AC |
ΔsubH° | 109.8 | kJ/mol | N/A | Colomina, Jimenez, et al., 1978 | DRB |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
109.8 ± 0.6 | 334.61 | V | Colomina, Jimenez, et al., 1978 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
28.330 | 456.70 | N/A | Sabbah and El Watik, 1992 | DH |
29.9 | 455.6 | DSC | Perlovich, Volkova, et al., 2008 | AC |
28.4 | 457.8 | N/A | Acree, 1991 | AC |
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
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.0 ± 0.2 | EI | Benoit, 1973 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7O+ | 12.8 ± 0.2 | COOH | EI | Benoit, 1973 | LLK |
C8H7O2+ | 12.5 ± 0.2 | OH | EI | Benoit, 1973 | LLK |
De-protonation reactions
C8H7O3- + =
By formula: C8H7O3- + H+ = C8H8O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1426. ± 8.8 | kJ/mol | G+TS | Yamdagni, McMahon, et al., 1974 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1397. ± 8.4 | kJ/mol | IMRE | Yamdagni, McMahon, et al., 1974 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, 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.
Colomina, Jimenez, et al., 1978
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of benzoic acid derivatives VII. Enthalpies of combustion and formation of the o-, m-, and p-methoxy-benzoic acids,
J. Chem. Thermodyn., 1978, 10, 661-665. [all data]
Alcolea P.M., 1994
Alcolea P.M.,
Spectroscopy of p-methoxybenzoic acid: an AM1 and ab initio study,
Appl. Spectrosc., 1994, 48, 27-36. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [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. (3), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [all data]
Anonymous, 1988
Anonymous, X.,
, NBS Spec. Publ. (U. S.) 260, 1988. [all data]
Marsh, 1987
Marsh, K.N.,
Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [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]
Perlovich, Volkova, et al., 2008
Perlovich, German L.; Volkova, Tatyana V.; Manin, Alex N.; Bauer-Brandl, Annette,
Extent and mechanism of solvation and partitioning of isomers of substituted benzoic acids: A thermodynamic study in the solid state and in solution,
J. Pharm. Sci., 2008, 97, 9, 3883-3896, https://doi.org/10.1002/jps.21260
. [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]
Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L.,
New reference materials for the calibration (temperature and energy) of differential thermal analysers and scanning calorimeters,
J. Therm. Anal., 1992, 38(4), 855-863. [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]
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]
Yamdagni, McMahon, et al., 1974
Yamdagni, R.; McMahon, T.B.; Kebarle, P.,
Substituent Effects on the Intrinsic Acidities of Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria Measurements,
J. Am. Chem. Soc., 1974, 96, 12, 4035, https://doi.org/10.1021/ja00819a063
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, 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 S°gas Entropy of gas at standard conditions 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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