Phenol
- Formula: C6H6O
- Molecular weight: 94.1112
- IUPAC Standard InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
- IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
- CAS Registry Number: 108-95-2
- 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. - Isotopologues:
- Other names: Carbolic acid; Baker's P and S Liquid and Ointment; Benzenol; Hydroxybenzene; Izal; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; PhOH; Benzene, hydroxy-; Acide carbolique; Baker's P & S liquid & Ointment; Fenol; Fenolo; NCI-C50124; Paoscle; Phenole; Carbolsaure; NA 2821; Phenol alcohol; Phenol, molten; Rcra waste number U188; UN 1671; UN 2312; UN 2821; Phenic alcohol; NSC 36808; Campho-Phenique Cold Sore Gel (Salt/Mix); Campho-Phenique Gel (Salt/Mix); Campho-Phenique Liquid (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -23.03 ± 0.14 | kcal/mol | Ccb | Cox, 1961 | ALS |
| ΔfH°gas | -23.05 ± 0.15 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
| ΔfH°gas | -22.5 | kcal/mol | N/A | Parks, Manchester, et al., 1954 | Value computed using ΔfHsolid° value of -162.8±1.0 kj/mol from Parks, Manchester, et al., 1954 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB |
| ΔfH°gas | -22.8 | kcal/mol | N/A | Badoche, 1941 | Value computed using ΔfHsolid° value of -163.9 kj/mol from Badoche, 1941 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.105 | 50. | Kudchadker S.A., 1978 | Recommended S(T) and Cp(T) values are in close agreement with statistical values calculated by [ Evans J.C., 1960, Green J.H.S., 1961]. Entropy value calculated by [ Sarin V.N., 1973] agrees well with the third-law entropy at 298.15 K but not at 400 K. Statistical values calculated by [ Ramaswamy V., 1970] seem to be erroneous.; GT |
| 9.890 | 100. | ||
| 12.95 | 150. | ||
| 16.65 | 200. | ||
| 22.61 | 273.15 | ||
| 24.670 | 298.15 | ||
| 24.823 | 300. | ||
| 32.455 | 400. | ||
| 38.697 | 500. | ||
| 43.614 | 600. | ||
| 47.524 | 700. | ||
| 50.703 | 800. | ||
| 53.344 | 900. | ||
| 55.566 | 1000. | ||
| 57.459 | 1100. | ||
| 59.082 | 1200. | ||
| 60.483 | 1300. | ||
| 61.692 | 1400. | ||
| 62.744 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas 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:
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 | -39.44 | kcal/mol | Ccb | Cox, 1961 | ALS |
| ΔfH°solid | -39.46 ± 0.30 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
| ΔfH°solid | -38.90 ± 0.25 | kcal/mol | Ccb | Parks, Manchester, et al., 1954 | ALS |
| ΔfH°solid | -39.18 | kcal/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-41.49 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -731. ± 3. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 34.419 | cal/mol*K | N/A | Andon, Counsell, et al., 1963 | DH |
| S°solid,1 bar | 34.11 | cal/mol*K | N/A | Parks, Huffman, et al., 1933 | Extrapolation below 90 K, 49.04 J/mol*K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 30.404 | 298.15 | Nichols and Wads, 1975 | DH |
| 47.75 | 313. | Rastorguev and Ganiev, 1967 | T = 313 to 373 K.; DH |
| 30.459 | 298.15 | Andon, Counsell, et al., 1963 | T = 13 to 336 K.; DH |
| 22.4 | 293. | Campbell and Campbell, 1940 | DH |
| 24.81 | 229.3 | Aoyama and Kanda, 1935 | T = 78 to 229 K. Value is unsmoothed experimental datum.; DH |
| 31.809 | 295.8 | Parks, Huffman, et al., 1933 | T = 93 to 296 K. Value is unsmoothed experimental datum.; DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Cox, 1961
Cox, J.D.,
The heats of combustion of phenol and the three cresols,
Pure Appl. Chem., 1961, 2, 125-128. [all data]
Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246-5254. [all data]
Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M.,
Heats of combustion and formation of some alcohols, phenols, and ketones,
J. Chem. Phys., 1954, 22, 2089-2090. [all data]
Badoche, 1941
Badoche, M.,
No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE.,
Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]
Kudchadker S.A., 1978
Kudchadker S.A.,
Ideal gas thermodynamic properties of phenol and cresols,
J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]
Evans J.C., 1960
Evans J.C.,
The vibrational spectra phenol and phenol-OD,
Spectrochim. Acta, 1960, 16, 1382-1392. [all data]
Green J.H.S., 1961
Green J.H.S.,
The thermodynamic properties of organic oxygen compounds. II. Vibrational assignment and calculated thermodynamic properties of phenol,
J. Chem. Soc., 1961, 2236-2241. [all data]
Sarin V.N., 1973
Sarin V.N.,
Thermodynamic properties in the gaseous state of certain monosubstituted benzenes,
Thermochim. Acta, 1973, 6, 39-46. [all data]
Ramaswamy V., 1970
Ramaswamy V.,
Thermo data for n-alkyl phenols,
Hydrocarbon Process., 1970, 49, 217-218. [all data]
Andon, Counsell, et al., 1963
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds,
Trans. Faraday Soc., 1963, 59, 830-835. [all data]
Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M.,
Thermal data on organic compounds. XI. The heat capacities,
entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]
Nichols and Wads, 1975
Nichols, N.; Wads, I.,
Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution,
J. Chem. Thermodynam., 1975, 7, 329-336. [all data]
Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A.,
Study of the heat capacity of selected solvents,
Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]
Campbell and Campbell, 1940
Campbell, A.N.; Campbell, A.J.R.,
The heats of solution, heats of formation,
specific heats and equilibrium diagrams of certain molecular compounds. J. Am. Chem. Soc., 1940, 62, 291-297. [all data]
Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E.,
Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature,
Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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