Benzene, (1-methylethyl)-
- Formula: C9H12
- Molecular weight: 120.1916
- IUPAC Standard InChI: InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3
- IUPAC Standard InChIKey: RWGFKTVRMDUZSP-UHFFFAOYSA-N
- CAS Registry Number: 98-82-8
- 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: Cumene; Cumol; Isopropylbenzene; 2-Phenylpropane; (1-Methylethyl)benzene; Isopropylbenzol; Benzene, isopropyl-; Cumeen; Isopropilbenzene; Isopropylbenzeen; Propane, 2-phenyl-; 2-Fenilpropano; 2-Fenyl-propaan; Rcra waste number U055; UN 1918; (Methylethyl)benzene; Benzene, i-propyl-; i-Propylbenzene; NSC 8776; iso-propylbenzene (cumene); (1-methylethyl)benzene (cumene)
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Reaction thermochemistry data
Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
C9H11- + =
By formula: C9H11- + H+ = C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1585. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1560. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
+
= (
•
)
By formula: NO- + C9H12 = (NO- • C9H12)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 189. | kJ/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M |
+
= (
•
)
By formula: Cl- + C9H12 = (Cl- • C9H12)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 23.0 | kJ/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 21. | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
+
=
By formula: H2 + C9H10 = C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -111.3 ± 2.1 | kJ/mol | Chyd | Abboud, Jimenez, et al., 1995 | liquid phase; solvent: Hyrocarbon; Like gas phase; ALS |
+
=
+
By formula: C9H11Cl + C6H6 = C6H5Cl + C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.59 ± 0.42 | kJ/mol | Eqk | Nesterova, Rozhnov, et al., 1985 | liquid phase; ALS |
+
=
+
By formula: C10H14 + C6H6 = C7H8 + C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.0 ± 0.6 | kJ/mol | Eqk | Tsvetkov, Rozhnov, et al., 1985 | liquid phase; ALS |
2 =
+
By formula: 2C9H12 = C12H18 + C6H6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1.5 ± 0.63 | kJ/mol | Eqk | Popov, Rozhnov, et al., 1974 | gas phase; ALS |
2 =
+
By formula: 2C9H12 = C6H6 + C12H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1.5 ± 0.59 | kJ/mol | Eqk | Popov, Rozhnov, et al., 1974 | gas phase; ALS |
3 +
=
By formula: 3H2 + C9H12 = C9H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -208. | kJ/mol | Eqk | Miki, 1975 | gas phase; GC; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F.,
Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-β- and β,β-methylated derivates,
J. Phys. Org. Chem., 1995, 8, 15-25. [all data]
Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N.,
Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements,
J. Chem. Thermodyn., 1985, 17, 649-656. [all data]
Tsvetkov, Rozhnov, et al., 1985
Tsvetkov, V.F.; Rozhnov, A.M.; Nesterova, T.N.,
Study of the equilibrium of isomerization and transalkylation of isopropyltoluenes,
Neftekhimiya, 1985, 53-57. [all data]
Popov, Rozhnov, et al., 1974
Popov, V.E.; Rozhnov, A.M.; Satronov, V.S.; Volkova, A.G.,
Disproportionation equilibrium for isopropylbenzene,
Neftekhimiya, 1974, 14, 364-367. [all data]
Miki, 1975
Miki, Y.,
The thermodynamic properties of C9H18 naphthenes. I. The determination of the equilibrium constants of the hydrogenation of propyl- and isopropylbenzene and ethyltoluenes,
Bull. Chem. Soc. Jpn., 1975, 48, 201-208. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature 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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