Benzene, pentamethyl-
- Formula: C11H16
- Molecular weight: 148.2447
- IUPAC Standard InChI: InChI=1S/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3
- IUPAC Standard InChIKey: BEZDDPMMPIDMGJ-UHFFFAOYSA-N
- CAS Registry Number: 700-12-9
- 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: Pentamethylbenzene; 1,2,3,4,5-Pentamethylbenzene; Benzene, 1,2,3,4,5-pentamethyl-
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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 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 | -16.1 ± 0.53 | kcal/mol | Ccb | Colomina, Jimenez, et al., 1989 | see Boned, Colomina, et al., 1964; ALS |
| ΔfH°gas | -13.8 | kcal/mol | N/A | Parks, West, et al., 1946 | Value computed using ΔfHsolid° value of -135.1±2.6 kj/mol from Parks, West, et al., 1946 and ΔsubH° value of 77.4 kj/mol from Colomina, Jimenez, et al., 1989.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 38.79 | 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 |
| 47.73 | 273.15 | ||
| 50.79 ± 0.1 | 298.15 | ||
| 51.00 | 300. | ||
| 63.19 | 400. | ||
| 74.43 | 500. | ||
| 84.20 | 600. | ||
| 92.59 | 700. | ||
| 99.78 | 800. | ||
| 106.0 | 900. | ||
| 111.3 | 1000. | ||
| 115.9 | 1100. | ||
| 119.8 | 1200. | ||
| 123.2 | 1300. | ||
| 126.2 | 1400. | ||
| 128.8 | 1500. |
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 by: 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
=
By formula: C11H16 = C11H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -32.6 ± 0.6 | kcal/mol | Ciso | Childs and Mulholland, 1983 | liquid phase |
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
View reactions leading to C11H16+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 203.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 196.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| <0.182 ± 0.013 | ECD | Wojnarovits and Foldiak, 1981 | EA is an upper limit: Chen and Wentworth, 1989,. G3MP2B3 calculations indicate an EA of ca. -0.5 eV, anion unbound.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.92 | PE | Howell, Goncalves, et al., 1984 | LBLHLM |
| 7.92 | PI | Bralsford, Harris, et al., 1960 | RDSH |
| 7.9 | CTS | Foster, 1959 | RDSH |
| 7.92 ± 0.02 | PI | Vilesov and Terenin, 1957 | RDSH |
| 7.92 | PE | Howell, Goncalves, et al., 1984 | Vertical value; LBLHLM |
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 | HP-5 | 100. | 1281.8 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
| Capillary | HP-5 | 120. | 1292.6 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
| Capillary | OV-101 | 100. | 1260. | Matisová, Kovacicová, et al., 1989 | He; Column length: 50. m; Column diameter: 0.20 mm |
| Capillary | Squalane | 100. | 1260. | Nabivach and Vasiliev, 1987 | |
| Capillary | OV-101 | 100. | 1260. | Gerasimenko and Nabivach, 1982 | N2; Column length: 50. m; Column diameter: 0.30 mm |
| Capillary | OV-101 | 120. | 1270. | Gerasimenko and Nabivach, 1982 | N2; Column length: 50. m; Column diameter: 0.30 mm |
| Capillary | OV-101 | 140. | 1280. | Gerasimenko and Nabivach, 1982 | N2; Column length: 50. m; Column diameter: 0.30 mm |
| Capillary | Squalane | 86. | 1253.9 | Macák, Nabivach, et al., 1982 | N2; Column length: 50. m; Column diameter: 0.25 mm |
| Capillary | Squalane | 96. | 1258.6 | Macák, Nabivach, et al., 1982 | N2; Column length: 50. m; Column diameter: 0.25 mm |
| Capillary | OV-101 | 100. | 1260.3 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
| Capillary | OV-101 | 120. | 1270.4 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
| Capillary | OV-101 | 140. | 1280.5 | Gerasimenko, Kirilenko, et al., 1981 | N2; Column length: 50. m; Column diameter: 0.3 mm |
| Capillary | Squalane | 86. | 1253.9 | Nabivach, Bur'yan, et al., 1978 | Column length: 50. m; Column diameter: 0.25 mm |
| Capillary | Squalane | 96. | 1258.6 | Nabivach, Bur'yan, et al., 1978 | Column length: 50. m; Column diameter: 0.25 mm |
| Capillary | Squalane | 100. | 1260. | Engewald and Wennrich, 1976 | N2; Column length: 100. m; Column diameter: 0.23 mm |
| Capillary | Squalane | 80. | 1251.20 | Soják and Rijks, 1976 | H2; Column length: 100. m; Column diameter: 0.25 mm |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1261. | Hayes and Pitzer, 1982 | 110. m/0.25 mm/0.20 μm, He, 1. K/min; Tstart: 35. C; Tend: 200. C |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH-100 | 1274.15 | Haagen-Smit Laboratory, 1997 | He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min) |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | ZB-Wax | 100. | 1644.5 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
| Capillary | ZB-Wax | 120. | 1666.7 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH | 1265.42 | White, Douglas, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
| Capillary | Petrocol DH | 1265.49 | White, Douglas, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
| Capillary | Petrocol DH | 1265. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
| Capillary | OV-101 | 1261. | Hayes and Pitzer, 1981 | 108. m/0.25 mm/0.2 μm, 1. K/min; Tstart: 35. C; Tend: 200. C |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | Squalane | 95.4 | 1249. | Sojak and Vigdergauz, 1978 | H2 |
| Capillary | Squalane | 130. | 1283. | Papazova and Pankova, 1975 | N2; Column length: 100. m; Column diameter: 0.25 mm |
| Packed | Polydimethyl siloxane | 110. | 1264. | Ferrand, 1962 |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 1287. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
| Capillary | Petrocol DH | 1268. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
| Capillary | OV-1 | 1269. | Orav, Kailas, et al., 1999 | 2. K/min; Tstart: 50. C; Tend: 160. C |
| Capillary | HP-5 | 1290.4 | Wang and Fingas, 1995 | 30. m/0.25 mm/0.25 μm, He, 35. C @ 2. min, 10. K/min, 300. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1261. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 218.10 | Wang, Fingas, et al., 1994 | 30. m/0.32 mm/0.25 μm, He, 50. C @ 2. min, 6. K/min; Tend: 300. C |
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.
Colomina, Jimenez, et al., 1989
Colomina, M.; Jimenez, P.; Roux, M.V.; Turrion, C.,
Thermochemical properties of 1,2,4,5-tetramethylbenzene, pentamethylbenzene, and hexamethylbenzene,
J. Chem. Thermodyn., 1989, 21, 275-281. [all data]
Boned, Colomina, et al., 1964
Boned, M.L.; Colomina, M.; Perez-Ossorio, R.; Turrion, C.,
Investigaciones termoquimicas sobre los polimetilbencenos superiores,
Anal. Fisc. Quim. B, 1964, 60, 459-468. [all data]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]
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]
Hastings S.H., 1957
Hastings S.H.,
Thermodynamic properties of selected methylbenzenes from 0 to 1000 K,
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Childs and Mulholland, 1983
Childs, R.F.; Mulholland, D.L.,
Thermochemical relationships between some bicyclohexenyl and benzenium cations,
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Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
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Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G.,
Electron capture detection of aromatic hydrocarbons,
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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]
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,
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Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Foster, 1959
Foster, R.,
Ionization potentials of electron donors,
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Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Pérez-Parajón, Santiuste, et al., 2004
Pérez-Parajón, J.M.; Santiuste, J.M.; Takács, J.M.,
Sensitivity of the methylbenzenes and chlorobenzenes retention index to column temperature, stationary phase polarity, and number and chemical nature of substituents,
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Matisová, Kovacicová, et al., 1989
Matisová, E.; Kovacicová, E.; Ha, P.T.; Kolek, E.; Engewald, W.,
Identification of alkylbenzenes up to C12 by capillary gas chromatography-mass spectrometry. II. Retention indices on OV-101 columns and retention-molecular structure correlations,
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Nabivach and Vasiliev, 1987
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Correlation dependencies of GC retention indices from physical chemical properties and structures of aromatic hydrocarbons,
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Gerasimenko and Nabivach, 1982
Gerasimenko, V.A.; Nabivach, V.M.,
Relationship between molecular structure and gas chromatographic retention of alkylbenzenes C8-C1 2 on polydimethylsiloxane,
Zh. Anal. Khim., 1982, 37, 110-116. [all data]
Macák, Nabivach, et al., 1982
Macák, J.; Nabivach, V.; Buryan, P.; Sindler, S.,
Dependence of retention indices of alkylbenzenes on their molecular structure,
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Gerasimenko, Kirilenko, et al., 1981
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Capillary gas chromatography of aromatic compounds found in coal tar fractions,
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Nabivach, Bur'yan, et al., 1978
Nabivach, V.M.; Bur'yan, P.; Matsak, I.,
Retention indices of aromatic hydrocarbons on a squalane capillary column,
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Engewald and Wennrich, 1976
Engewald, W.; Wennrich, L.,
Molekülstruktur und Retentionsverhalten. VIII. Zum Retentionsverhalten höherer Alkylbenzole bei der Gas-Verteilungs-Chromatographie,
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Soják and Rijks, 1976
Soják, L.; Rijks, J.A.,
Capillary gas chromatography of alkylbenzenes. I. Some problems encountered with the precision of the retention indcies of alkylbenzenes,
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Hayes and Pitzer, 1982
Hayes, P.C., Jr.; Pitzer, E.W.,
Characterizing petroleum- and shale-derived jet fuel distillates via temperature-programmed Kováts indices,
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Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory,
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White, C.M.; Douglas, L.J.; Hackett, J.P.; Anderson, R.R.,
Characterization of synthetic gasoline from the chloromethane-zeolite reaction,
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Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
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Kovats indices as a tool in characterizing hydrocarbon fuels in temperature programmed glass capillary gas chromatography. Part 1. Qualitative identification, Inhouse rpt. for Air Force Wright Aeronautical Labs., Air Force Wright Aeronautical Labs., Wright-Patterson AFB, Ohio, 1981, 75. [all data]
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Sojak, L.; Vigdergauz, M.S.,
Comparison of interpolation methods for the interpretation of retention data in gas chromatography,
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Papazova, D.I.; Pankova, M.C.,
Identification of individual aromatic hydrocarbons in kerosene fraction (b.p. 150-250 °),
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Ferrand, R.,
Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products,
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Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Supelco, 2012
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Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
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Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J.,
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Wang, Z.; Fingas, M.,
Differentiation of the source of spilled oil and monitoring of the oil weathering process using gas chromatography-mass spectrometry,
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Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Wang, Fingas, et al., 1994
Wang, Z.; Fingas, M.; Li, K.,
Fractionation of a light crude oil and identification and quantitation of aliphatic, aromatic, and biomarker comopunds by GC-FID and GC-MS, Part II,
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. [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:
Cp,gas Constant pressure heat capacity of gas EA Electron affinity ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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