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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 0.94 ± 0.26 | kcal/mol | Ccb | Prosen, Gilmont, et al., 1945 | Hf by Prosen, Johnson, et al., 1946; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 92.383 | cal/mol*K | N/A | Kishimoto K., 1973 | GT |
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 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°liquid | -9.85 ± 0.26 | kcal/mol | Ccb | Prosen, Gilmont, et al., 1945 | Hf by Prosen, Johnson, et al., 1946; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1246.52 ± 0.23 | kcal/mol | Ccb | Prosen, Gilmont, et al., 1945 | Hf by Prosen, Johnson, et al., 1946; Corresponding ΔfHºliquid = -9.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1247.3 | kcal/mol | Ccb | Richards and Barry, 1915 | At 291 K; Corresponding ΔfHºliquid = -9.08 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 66.341 | cal/mol*K | N/A | Kishimoto, Suga, et al., 1973 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 51.24 | 295.96 | Andolenko and Grigor'ev, 1979 | T = 296 to 413 K. Unsmoothed experimental datum given as 1.784 kJ/kg*K.; DH |
| 51.482 | 298.15 | Kishimoto, Suga, et al., 1973 | T = 14 to 314 K. Glass, 14 to 126 K.; DH |
| 50.050 | 299.8 | Schlinger and Sage, 1952 | T = 300 to 366 K.; DH |
| 50.91 | 298. | Kurbatov, 1947 | T = 16 to 153°C, mean Cp, four temperatures.; DH |
| 47.49 | 302.0 | de Kolossowsky and Udowenko, 1934 | DH |
| 47.49 | 302.0 | Kolosovskii and Udovenko, 1934 | DH |
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
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° | 378.9 ± 2.1 | kcal/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° | 372.9 ± 2.0 | kcal/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° | 45.1 | kcal/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° | 5.50 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 5.0 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
+
=
By formula: H2 + C9H10 = C9H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26.60 ± 0.50 | kcal/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° | -0.14 ± 0.10 | kcal/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 ± 0.1 | kcal/mol | Eqk | Tsvetkov, Rozhnov, et al., 1985 | liquid phase; ALS |
2 =
+
By formula: 2C9H12 = C12H18 + C6H6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.37 ± 0.15 | kcal/mol | Eqk | Popov, Rozhnov, et al., 1974 | gas phase; ALS |
2 =
+
By formula: 2C9H12 = C6H6 + C12H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 0.37 ± 0.14 | kcal/mol | Eqk | Popov, Rozhnov, et al., 1974 | gas phase; ALS |
3 +
=
By formula: 3H2 + C9H12 = C9H18
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -49.8 | kcal/mol | Eqk | Miki, 1975 | gas phase; GC; ALS |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
| k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 0.087 | 3200. | X | N/A | |
| 0.068 | Q | N/A | Several references are given in the list of Henry's law constants but not assigned to specific species. | |
| 0.068 | Q | N/A | missing citation give several references for the Henry's law constants but don't assign them to specific species. | |
| 0.78 | L | N/A | ||
| 0.068 | V | N/A |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Prosen, Gilmont, et al., 1945
Prosen, E.J.; Gilmont, R.; Rossini, F.D.,
Heats of combustion of benzene, toluene, ethyl-benzene, o-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene,
J. Res. NBS, 1945, 34, 65-70. [all data]
Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heats of combustion and formation at 25°C of the alkylbenzenes through C10H14, and of the higher normal monoalkylbenzenes,
J. Res. NBS, 1946, 36, 455-461. [all data]
Kishimoto K., 1973
Kishimoto K.,
Calorimetric study of the glassy state. VIII. Heat capacity and relaxational phenomena of isopropylbenzene,
Bull Chem. Soc. Japan, 1973, 46, 3020-3031. [all data]
Richards and Barry, 1915
Richards, T.W.; Barry, F.,
The heats of combustion of aromatic hydrocarbons and hexamethylene,
J. Am. Chem. Soc., 1915, 37, 993-1020. [all data]
Kishimoto, Suga, et al., 1973
Kishimoto, K.; Suga, H.; Syuzo, S.,
Calorimetric study of the glassy state. VIII. Heat capacity and relaxational phenomena of isopropylbenzene,
Bull. Chem. Soc. Japan, 1973, 46, 3020-3031. [all data]
Andolenko and Grigor'ev, 1979
Andolenko, R.A.; Grigor'ev, B.A.,
Investigation of isobaric heat capacity of aromatic hydrocarbons at atmospheric pressure, Iaz. Vyssh. Ucheb. Zaved.,
Neft i Gaz (11), 1979, 78, 90. [all data]
Schlinger and Sage, 1952
Schlinger, W.G.; Sage, B.H.,
Isobaric heat capacities at bubble point. cis-2-butene, isopropylbenzene, and n-decane,
Ind. Eng. Chem., 1952, 44, 2454-2456. [all data]
Kurbatov, 1947
Kurbatov, V.Ya.,
Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons,
Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]
de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W.,
Determination des chaleurs specifiques des liquides,
Compt. rend., 1934, 198, 1394-1395. [all data]
Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W.,
Specific heat of liquids. II.,
Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions T Temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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