Benzoic acid, 4-methyl-
- Formula: C8H8O2
- Molecular weight: 136.1479
- IUPAC Standard InChI: InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)
- IUPAC Standard InChIKey: LPNBBFKOUUSUDB-UHFFFAOYSA-N
- CAS Registry Number: 99-94-5
- 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: p-Toluic acid; p-Methylbenzoic acid; p-Toluylic acid; Crithminic acid; 4-Methylbenzoic acid; 4-Toluic acid; para-Toluic acid; NSC 2215; p-Carboxytoluene; p-Tolylcarboxylic acid
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Gas phase thermochemistry 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 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 | -330.4 ± 1.5 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1986 | see Colomina, Boned, et al., 1961; ALS |
| ΔfH°gas | -330.4 | kJ/mol | N/A | Corral, 1960 | Value computed using ΔfHsolid° value of -429.2±1.1 kj/mol from Corral, 1960 and ΔsubH° value of 98.8 kj/mol from Colomina, Jimenez, et al., 1986.; DRB |
| ΔfH°gas | -324.5 | kJ/mol | N/A | Breitenbach and Derkosch, 1951 | Value computed using ΔfHsolid° value of -423.3±3.8 kj/mol from Breitenbach and Derkosch, 1951 and ΔsubH° value of 98.8 kj/mol from Colomina, Jimenez, et al., 1986.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas 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 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 | -429.2 ± 1.5 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1986 | see Colomina, Boned, et al., 1961; ALS |
| ΔfH°solid | -429.2 ± 1.1 | kJ/mol | Ccb | Corral, 1960 | Different experiments; ALS |
| ΔfH°solid | -423.3 ± 3.8 | kJ/mol | Ccb | Breitenbach and Derkosch, 1951 | Reanalyzed by Cox and Pilcher, 1970, Original value = -422.6 kJ/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3862.3 ± 0.9 | kJ/mol | Ccb | Colomina, Jimenez, et al., 1986 | see Colomina, Boned, et al., 1961; Corresponding ΔfHºsolid = -429.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3862.3 ± 0.92 | kJ/mol | Ccb | Corral, 1960 | Different experiments; Corresponding ΔfHºsolid = -429.15 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -3868. | kJ/mol | Ccb | Breitenbach and Derkosch, 1951 | Corresponding ΔfHºsolid = -423.4 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 |
|---|---|---|---|
| 169.0 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 225 C.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 547.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 455. | K | N/A | Sugunan and Thomas, 1993 | Uncertainty assigned by TRC = 2. K; TRC |
| Tfus | 450.15 | K | N/A | Ipatieff, Corson, et al., 1936 | Uncertainty assigned by TRC = 2.5 K; TRC |
| Tfus | 452.8 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 98.6 ± 0.6 | kJ/mol | ME | Monte, Almeida, et al., 2004 | Based on data from 320. to 337. K.; AC |
| ΔsubH° | 98.8 ± 0.3 | kJ/mol | ME | Colomina, Jimenez, et al., 1986, 2 | Based on data from 318. to 337. K.; AC |
| ΔsubH° | 98.8 ± 0.3 | kJ/mol | V | Colomina, Jimenez, et al., 1986 | see Colomina, Boned, et al., 1961; ALS |
| ΔsubH° | 98.8 | kJ/mol | N/A | Colomina, Jimenez, et al., 1986 | DRB |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 22.72 | 452.8 | Acree, 1991 | AC |
| 22.720 | 452.8 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 50.2 | 452.8 | Andrews, Lynn, et al., 1926 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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., 1986
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Propiedades termoquimicas de derivados del acido benzoico. XIII. Presiones de vapor y entalpias de sublimacion y formacion de los acidos toluicos,
An. Quim., 1986, 82, 126-130. [all data]
Colomina, Boned, et al., 1961
Colomina, M.; Boned, M.L.; Turrion, C.,
Investigaciones termoquimicas sobre los acidos alquilbenzoicos. I. Acidos toluicos,
An. Fis. Quim., 1961, 57, 655-664. [all data]
Corral, 1960
Corral, L.B.,
Investigaciones termoquimicas sobre los acidos toluicos y dimetilbenzoicos,
Rev. R. Acad. Cienc., 1960, 54, 365-403. [all data]
Breitenbach and Derkosch, 1951
Breitenbach, J.W.; Derkosch, J.,
Verbrennungswarmen von peroxyden und verwandten verbindungen sowie von polystrolen,
Monatsh. Chem., 1951, 82, 177-179. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Sugunan and Thomas, 1993
Sugunan, S.; Thomas, B.,
Salting Coefficients of 2-, 3-, and 4-Methylbenzoic Acids,
J. Chem. Eng. Data, 1993, 38, 520-1. [all data]
Ipatieff, Corson, et al., 1936
Ipatieff, V.N.; Corson, B.B.; Pines, H.,
Influence of Sulfuric Acid Concentration upon Reaction between Olefins and Benzene,
J. Am. Chem. Soc., 1936, 58, 919-22. [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]
Monte, Almeida, et al., 2004
Monte, Manuel J.S.; Almeida, Ana R.R.P.; Ribeiro da Silva, Manuel A.V.,
Thermodynamic study of the sublimation of eight 4-n-alkylbenzoic acids,
The Journal of Chemical Thermodynamics, 2004, 36, 5, 385-392, https://doi.org/10.1016/j.jct.2004.02.001
. [all data]
Colomina, Jimenez, et al., 1986, 2
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Propiedades termoquimicas de derivados del acido benzoico. XIII. Presiones de vapor y entalpias de sublimacion y formacion de los acidos toluicos,
An. Quim., 1986, 82, 126. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point 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 ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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