Benzene, 1,2,3,5-tetramethyl-
- Formula: C10H14
- Molecular weight: 134.2182
- IUPAC Standard InChI: InChI=1S/C10H14/c1-7-5-8(2)10(4)9(3)6-7/h5-6H,1-4H3
- IUPAC Standard InChIKey: BFIMMTCNYPIMRN-UHFFFAOYSA-N
- CAS Registry Number: 527-53-7
- 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: Isodurene; 1,2,3,5-Tetramethylbenzene
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Gas phase thermochemistry data
Go To: Top, Condensed 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -43.2 ± 1.3 | kJ/mol | Ccb | Draeger, 1985 | Unpublished measurement of W.D.Good; ALS |
| ΔfH°gas | -44.4 ± 1.2 | kJ/mol | N/A | Good, 1975 | Value computed using ΔfHliquid° value of -96.4±1.2 kj/mol from Good, 1975 and ΔvapH° value of 52.0±0.17 kj/mol from missing citation.; DRB |
| ΔfH°gas | -46.5 ± 3.0 | kJ/mol | N/A | Prosen, Johnson, et al., 1946 | Value computed using ΔfHliquid° value of -98.5±3 kj/mol from Prosen, Johnson, et al., 1946 and ΔvapH° value of 52.0±0.17 kj/mol from missing citation.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 135.0 | 200. | Draeger, 1985 | There is an appreciable difference between values of S(T) and Cp(T) for tetra-, penta-, and hexamethylbenzene from earlier statistical thermodynamics calculation [ Hastings S.H., 1957] and those obtained by [ Draeger, 1985] (up to 5, 9, and 16 J/mol*K, respectively). Results [ Draeger, 1985] are more reliable and they agree with experimental data for hexamethylbenzene.; GT |
| 168.8 | 273.15 | ||
| 180.7 ± 0.4 | 298.15 | ||
| 181.6 | 300. | ||
| 229.3 | 400. | ||
| 273.0 | 500. | ||
| 310.6 | 600. | ||
| 342.6 | 700. | ||
| 369.8 | 800. | ||
| 393.0 | 900. | ||
| 413.0 | 1000. | ||
| 430.1 | 1100. | ||
| 444.9 | 1200. | ||
| 457.7 | 1300. | ||
| 468.7 | 1400. | ||
| 478.3 | 1500. |
Condensed phase thermochemistry 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:
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 | -96.4 ± 1.2 | kJ/mol | Ccb | Good, 1975 | ALS |
| ΔfH°liquid | -98.5 ± 3.0 | kJ/mol | Ccb | Prosen, Johnson, et al., 1946 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -5839.6 ± 1.1 | kJ/mol | Ccb | Good, 1975 | Corresponding ΔfHºliquid = -96.36 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -5837.5 ± 3.0 | kJ/mol | Ccb | Prosen, Johnson, et al., 1946 | Corresponding ΔfHºliquid = -98.41 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -5815.3 ± 5.9 | kJ/mol | Ccb | Banse and Parks, 1933 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5811.20 kJ/mol; Corresponding ΔfHºliquid = -120.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 310.0 | J/mol*K | N/A | Huffman, Parks, et al., 1931 | Extrapolation below 90 K, 80.54 J/mol*K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 240.2 | 297.1 | Huffman, Parks, et al., 1931 | T = 92 to 297 K. Value is unsmoothed experimental datum.; DH |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 845.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 816.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| <0.108 ± 0.013 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.1 eV, anion unbound.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.47 ± 0.05 | EI | Meyer and Harrison, 1964 | RDSH |
| 8.07 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
| 8.3 ± 0.03 | PE | Klessinger, 1972 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Draeger, 1985
Draeger, J.A.,
The methylbenzenes II. Fundamental vibrational shifts, statistical thermodynamic functions, and properties of formation,
J. Chem. Thermodyn., 1985, 17, 263-275. [all data]
Good, 1975
Good, W.D.,
The standard enthalpies of combustion and formation of n-butylbenzene, the dimethylethylbenzenes, and the tetramethylbenzenes in the condensed state,
J. Chem. Thermodyn., 1975, 7, 49-59. [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]
Hastings S.H., 1957
Hastings S.H.,
Thermodynamic properties of selected methylbenzenes from 0 to 1000 K,
J. Phys. Chem., 1957, 61, 730-735. [all data]
Banse and Parks, 1933
Banse, H.; Parks, G.S.,
Thermal data on organic compounds. XII. The heats of combustion of nine hydrocarbons,
J. Am. Chem. Soc., 1933, 55, 3223-3227. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M.,
Thermal data on organic compounds. X. Further studies on the heat capacities, entropies and free energies of hydrocarbons,
J. Am. Chem. Soc., 1931, 53, 3876-3888. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
J. Chromatogr. Sci., 1981, 206, 511. [all data]
Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E.,
Experimental Determination of Electron Affinities of Organic Molecules,
Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]
Meyer and Harrison, 1964
Meyer, F.; Harrison, A.G.,
Ionization potentials of methyl-substituted benzenes and cyclopentadienes,
Can. J. Chem., 1964, 42, 2256. [all data]
Howell, Goncalves, et al., 1984
Howell, J.O.; Goncalves, J.M.; Amatore, C.; Klasinc, L.; Wightman, R.M.; Kochi, J.K.,
Electron transfer from aromatic hydrocarbons and their π-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials,
J. Am. Chem. Soc., 1984, 106, 3968. [all data]
Klessinger, 1972
Klessinger, M.,
Ionization potentials of substituted benzenes,
Angew. Chem. Int. Ed. Engl., 1972, 11, 525. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity S°liquid Entropy of liquid at standard conditions 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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