p-Cumenol
- Formula: C9H12O
- Molecular weight: 136.1910
- IUPAC Standard InChIKey: YQUQWHNMBPIWGK-UHFFFAOYSA-N
- CAS Registry Number: 99-89-8
- 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: 4-Isopropylphenol; Phenol, 4-(1-methylethyl)-; Phenol, p-isopropyl-; p-Isopropylphenol; Australol; 4-(1-Methylethyl)phenol; 1-Hydroxy-4-isopropylbenzene; Prodox 133; NSC 1888; p-Cuminol
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -175.3 ± 2.4 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | Author was aware that data differs from previously reported values; Isomerization |
ΔfH°gas | -183.9 | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -270. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -4983. | kJ/mol | Ccb | Bertholon, Giray, et al., 1971 | Corresponding ΔfHºsolid = -270. kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -4977. ± 13. | kJ/mol | Ccb | Bertholon, 1967 | Corresponding ΔfHºsolid = -280. kJ/mol (simple calculation by NIST; no Washburn corrections) |
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:
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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 500. ± 4. | K | AVG | N/A | Average of 12 out of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 334. ± 2. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 88.07 | kJ/mol | C | Bertholon, Giray, et al., 1971 | ALS |
ΔsubH° | 86.1 | kJ/mol | N/A | Bertholon, Giray, et al., 1971 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.7 | 406. | EB | Nesterova, Nazmutdinov, et al., 1990 | Based on data from 391. to 507. K.; AC |
63.1 | 395. | A | Stephenson and Malanowski, 1987 | Based on data from 380. to 496. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
381.3 to 501.4 | 5.77683 | 2801.531 | -15.386 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
56. ± 2. | 223.0 ± 0.5 | V | Bertholon, 1967 | ALS |
Reaction 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C9H11O- + =
By formula: C9H11O- + H+ = C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1461. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1433. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale; B |
By formula: C6H6O + C12H18O = C9H12O + C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -0.7 ± 1.0 | kJ/mol | Eqk | Nesterova, Pimerzin, et al., 1989 | liquid phase; Isomerization; ALS |
ΔrH° | -0.7 ± 1.0 | kJ/mol | Eqk | Nesterova, Pilyshchikov, et al., 1983 | liquid phase; GC; ALS |
By formula: C9H12O = C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.42 ± 0.29 | kJ/mol | Eqk | Nesterova, Pilyshchikov, et al., 1983 | liquid phase; GC; ALS |
By formula: C9H12O = C9H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.95 ± 0.21 | kJ/mol | Eqk | Nesterova, Pilyshchikov, et al., 1983 | liquid phase; GC; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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 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° | 1461. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1433. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; ΔHf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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]
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]
von Terres, Gebert, et al., 1955
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]
Nesterova, Pilyshchikov, et al., 1983
Nesterova, T.N.; Pilyshchikov, V.A.; Rozhnov, A.M.,
Chemical Equilibrium in the system isopropylphenols-phenol,
J. Appl. Chem. USSR, 1983, 56, 1257-1261. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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