Phenol, 3-(1-methylethyl)-
- Formula: C9H12O
- Molecular weight: 136.1910
- IUPAC Standard InChI: InChI=1S/C9H12O/c1-7(2)8-4-3-5-9(10)6-8/h3-7,10H,1-2H3
- IUPAC Standard InChIKey: VLJSLTNSFSOYQR-UHFFFAOYSA-N
- CAS Registry Number: 618-45-1
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Phenol, m-isopropyl-; m-Cumenol; m-Isopropylphenol; 3-Isopropylphenol; 3-(1-Methylethyl)phenol; Isopropylphenol, meta; 3-isopropylhydroxybenzene
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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 | -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 | -45.55 | kcal/mol | Ccb | Bertholon, Giray, et al., 1971 | see Bertholon, 1967 |
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° | 349.0 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 342.2 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
=
By formula: C9H12O = C9H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.339 ± 0.069 | kcal/mol | Eqk | Nesterova, Pilyshchikov, et al., 1983 | liquid phase; GC; ALS |
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 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° | 349.0 ± 2.1 | 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° | 342.2 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | PS-255 | 150. | 1207. | Engewald, Billing, et al., 1988 | 50. m/0.30 mm/0.25 μm |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1227.3 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 1C/min => |
| Capillary | VF-5MS | 1227.9 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 2C/min => |
| Capillary | VF-5MS | 1229.2 | Mjøs, Meier, et al., 2006 | 50. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 30C/min => 100C => 4C/min => |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxane, unknown content of Ph-groups | 1228. | Geldon, 1989 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
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]
Engewald, Billing, et al., 1988
Engewald, W.; Billing, U.; Topalova, I.; Petsev, N.,
Structure-retention correlations of alkylphenols in gas-liquid and gas-solid chromatography,
J. Chromatogr., 1988, 446, 71-77, https://doi.org/10.1016/S0021-9673(00)94419-4
. [all data]
Mjøs, Meier, et al., 2006
Mjøs, S.A.; Meier, S.; Boitsov, S.,
Alkylphenol retention indices,
J. Chromatogr. A, 2006, 1123, 1, 98-105, https://doi.org/10.1016/j.chroma.2006.05.002
. [all data]
Geldon, 1989
Geldon, A.L.,
Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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