Phenol, 2-(1-methylethyl)-
- Formula: C9H12O
- Molecular weight: 136.1910
- IUPAC Standard InChIKey: CRBJBYGJVIBWIY-UHFFFAOYSA-N
- CAS Registry Number: 88-69-7
- 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: Phenol, o-isopropyl-; o-Isopropylphenol; 2-Isopropylphenol; 2-(1-Methylethyl)phenol; o-Cumenol; Isopropylphenol, ortho; 1-Hydroxy-2-isopropylbenzene; Prodox 131; o-Hydroxycumene; NSC 5103
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -41.90 ± 0.57 | kcal/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | Author was aware that data differs from previously reported values; Isomerization |
ΔfH°gas | -38.55 | kcal/mol | Ccb | Bertholon, Giray, et al., 1971 | see Bertholon, 1967 |
Phase change data
Go To: Top, Gas phase thermochemistry 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 487. ± 2. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 290.00 | K | N/A | Bertholon, 1967, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 288.65 | K | N/A | Karr, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 288.65 | K | N/A | von Terres, Gebert, et al., 1955 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 288.65 | K | N/A | Stull, 1947 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 17.45 | kcal/mol | C | Bertholon, Giray, et al., 1971 | see Bertholon, 1967; ALS |
ΔvapH° | 16.4 | kcal/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.2 | 390. | EB | Nesterova, Nazmutdinov, et al., 1990 | Based on data from 375. to 493. K.; AC |
13.2 | 385. | A | Stephenson and Malanowski, 1987 | Based on data from 370. to 489. K.; AC |
13.4 | 390. | N/A | Tsvetkov, Nazmutdinov, et al., 1986 | Based on data from 375. to 493. K.; AC |
13.7 | 350. | N/A | Stull, 1947, 2 | Based on data from 335. to 501. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.8 to 487.7 | 5.65842 | 2657.919 | -17.436 | von Terres, Gebert, et al., 1955, 2 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics 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 by: John E. Bartmess
View reactions leading to C9H12O+ (ion structure unspecified)
De-protonation reactions
C9H11O- + =
By formula: C9H11O- + H+ = C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 347.5 ± 2.2 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 340.0 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
References
Go To: Top, Gas 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.
Nesterova, Pimerzin, et al., 1989
Nesterova, T.N.; Pimerzin, A.A.; Rozhnov, A.M.; Karlina, T.N.,
Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols,
J. Chem. Thermodyn., 1989, 21, 385-395. [all data]
Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F.,
No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols,
Bull. Soc. Chim. France, 1971, 3180-3187. [all data]
Bertholon, 1967
Bertholon, G.,
No. 534. - Etude physicochimique des phonols. VI. - Etude physicochimique des trois isopropylphenols isomeres,
Bull. Soc. Chim. France, 1967, 8, 2977-2982. [all data]
Bertholon, 1967, 2
Bertholon, G.,
Physicochemical study of the phenols. VI. Physicochemical study of three isomeric isopropylphenols.,
Bull. Soc. Chim. Fr., 1967, No. 8, 2977. [all data]
Karr, 1957
Karr, C.,
, U. S. Bur. Mines, Inform. Circ. IC 7802, 1957. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Brennst.-Chem., 1955, 36, 272. [all data]
Stull, 1947
Stull, D.R.,
Organic compounds,
Ind. Eng. Chem., 1947, 39, 517. [all data]
Nesterova, Nazmutdinov, et al., 1990
Nesterova, T.N.; Nazmutdinov, A.G.; Tsvetkov, V.S.; Rozhnov, A.M.; Roshchupkina, I. Yu,
Vapour pressures and enthalpies of vaporization of alkylphenols,
The Journal of Chemical Thermodynamics, 1990, 22, 4, 365-377, https://doi.org/10.1016/0021-9614(90)90122-7
. [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]
Tsvetkov, Nazmutdinov, et al., 1986
Tsvetkov, V.S.; Nazmutdinov, A.G.; Sharonov, K.S.; Rozhnov, A.M.,
Termodin. Org. Soedin., 1986, 71. [all data]
Stull, 1947, 2
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
von Terres, Gebert, et al., 1955, 2
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten,
Brennst.-Chem., 1955, 36, 272-274. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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