Benzene, hexamethyl-

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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
Δfgas-18.5 ± 0.60kcal/molCcbColomina, Jimenez, et al., 1989see Boned, Colomina, et al., 1964; ALS
Δfgas-18.7kcal/molN/AParks, West, et al., 1946Value computed using ΔfHsolid° value of -163.3±3.1 kj/mol from Parks, West, et al., 1946 and ΔsubH° value of 85.0 kj/mol from Parks, West, et al., 1946.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
44.07200.Draeger, 1985Recommended values are in close agreement with experimental data on S(T). Discrepancies with earlier statistically calculated values [ Hastings S.H., 1957] amount to 16 and 13 J/mol*K in S(T) and Cp(T), respectively.; GT
54.33273.15
57.72 ± 0.1298.15
57.98300.
71.30400.
83.48500.
94.12600.
103.3700.
111.1800.
117.9900.
123.81000.
128.81100.
133.21200.
137.01300.
140.21400.
143.11500.

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
Δfliquid-33.94kcal/molCcbOth, 1968ALS
Quantity Value Units Method Reference Comment
Δcliquid-1705.2 ± 1.7kcal/molCcbBanse and Parks, 1933Reanalyzed by Cox and Pilcher, 1970, Original value = -1703.88 kcal/mol; Corresponding Δfliquid = -38.25 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Δfsolid-38.81 ± 0.60kcal/molCcbColomina, Jimenez, et al., 1989see Boned, Colomina, et al., 1964; ALS
Δfsolid-39.03 ± 0.73kcal/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -39.19 ± 0.02 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcsolid-1704.6 ± 0.45kcal/molCcbColomina, Jimenez, et al., 1989see Boned, Colomina, et al., 1964; Corresponding Δfsolid = -38.81 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1700.1 ± 1.3kcal/molCcbHoldiness, 1984Hf NR; Corresponding Δfsolid = -43.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-1704.42 ± 0.72kcal/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -1704.29 ± 0.68 kcal/mol; Corresponding Δfsolid = -39.03 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar72.373cal/mol*KN/AAtake, Gyoten, et al., 1982DH
solid,1 bar73.210cal/mol*KN/AFrankosky and Aston, 1965crystaline, I phase; DH
solid,1 bar74.00cal/mol*KN/AHuffman, Parks, et al., 1930crystaline, I phase; Extrapolation below 90 K, 82.38 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
88.60455.Kurbatov, 1947T = 183 to 256°C, mean Cp, two temperatures.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
58.17298.15Colomina, Jimenez, et al., 1989DH
60.256300.Atake, Gyoten, et al., 1982T = 3 to 300 K.; DH
58.709298.15Frankosky and Aston, 1965crystaline, I phase; T = 13 to 340 K.; DH
61.21293.81Momotani, Suga, et al., 1956T = 273 to 443 K. Unsmoothed experimental datum.; DH
61.78303.Spaght, Thomas, et al., 1932crystaline, II phase; T = 30 to 200°C.; DH
60.90294.6Huffman, Parks, et al., 1930crystaline, I phase; T = 85 to 294 K. Value is unsmoothed experimental datum.; DH

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil538.2KN/AWeast and Grasselli, 1989BS
Tboil536.85KN/ACooper, Crowne, et al., 1967Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Tfus438. ± 3.KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tc758. ± 1.KN/ATsonopoulos and Ambrose, 1995 
Tc758.KN/AAmbrose, Broderick, et al., 1974Uncertainty assigned by TRC = 2. K; TRC
Tc751.15KN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 10. K; crit. temp. greater than this - sample decomposes at this T; TRC
Quantity Value Units Method Reference Comment
Δvap16.4kcal/molCGCZhao, Unhannanant, et al., 2008AC
Quantity Value Units Method Reference Comment
Δsub20. ± 2.kcal/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
13.6458.AStephenson and Malanowski, 1987Based on data from 443. to 537. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
20.4320.AAmbrose, Lawrenson, et al., 1976Based on data from 303. to 338. K.; AC
19.9329.AOverberger, Steele, et al., 1969Based on data from 314. to 364. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
4.931438.7Domalski and Hearing, 1996See also Spaght, Thomas, et al., 1931.; AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
1.09383.7Domalski and Hearing, 1996CAL
11.24438.7

Temperature of phase transition

Ttrs (K) Initial Phase Final Phase Reference Comment
382.crystaline, IIIcrystaline, IFujiwara, Inaba, et al., 1992DH
439.crystaline, IliquidFujiwara, Inaba, et al., 1992DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.2629117.5crystaline, IIIcrystaline, IIFujiwara, Inaba, et al., 1992From Atake, Gyoten, et al., 1982; DH
0.3585384.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
0.2636115.5crystaline, IIcrystaline, IYoshimoto, Fujiwara, et al., 1985DH
0.237117.5crystaline, IIIcrystaline, IIAtake, Gyoten, et al., 1982First order transition.; DH
0.26969116.48crystaline, IIcrystaline, IFrankosky and Aston, 1965Entropy obtained as difference of integral of observed Cp over range 115 to 128 K, and integral of extrapolated Cp data.; DH
0.4400383.55crystaline, IIcrystaline, IMomotani, Suga, et al., 1956DH
4.9199438.35crystaline, IliquidMomotani, Suga, et al., 1956DH
0.4221383.7crystaline, IIcrystaline, ISpaght, Thomas, et al., 1932DH
4.9331438.7crystaline, IliquidSpaght, Thomas, et al., 1932DH
0.2431108.crystaline, IIIcrystaline, IIHuffman, Parks, et al., 1930DH
0.0370151.crystaline, IIcrystaline, IHuffman, Parks, et al., 1930DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
2.2117.5crystaline, IIIcrystaline, IIFujiwara, Inaba, et al., 1992From; DH
0.93384.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
2.28115.5crystaline, IIcrystaline, IYoshimoto, Fujiwara, et al., 1985DH
2.0117.5crystaline, IIIcrystaline, IIAtake, Gyoten, et al., 1982First; DH
2.409116.48crystaline, IIcrystaline, IFrankosky and Aston, 1965Entropy; DH
1.15383.55crystaline, IIcrystaline, IMomotani, Suga, et al., 1956DH
11.20438.35crystaline, IliquidMomotani, Suga, et al., 1956DH
1.10383.7crystaline, IIcrystaline, ISpaght, Thomas, et al., 1932DH
11.2438.7crystaline, IliquidSpaght, Thomas, et al., 1932DH
2.3108.crystaline, IIIcrystaline, IIHuffman, Parks, et al., 1930DH
0.24151.crystaline, IIcrystaline, IHuffman, Parks, et al., 1930DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

Hexamethyltetracyclo[2.2.0(2,6).0(3,5)]hexane = Benzene, hexamethyl-

By formula: C12H18 = C12H18

Quantity Value Units Method Reference Comment
Δr-82.5 ± 0.8kcal/molCmAdam and Chang, 1969liquid phase; solvent: Pure phase; Heat of isomerization; ALS
Δr-91.2kcal/molEqkOth, 1968liquid phase; Heat of isomerization, see Oth, 1969; ALS
Δr-91.5kcal/molCmOth, 1968liquid phase; solvent: Toluene-d8; Heat of isomerization at 150°C; ALS

Dewar benzene, hexamethyl- = Benzene, hexamethyl-

By formula: C12H18 = C12H18

Quantity Value Units Method Reference Comment
Δr-56.2 ± 0.6kcal/molCmAdam and Chang, 1969liquid phase; solvent: Pure phase; ALS
Δr-59.5kcal/molEqkOth, 1968liquid phase; Heat of isomerization, see Oth, 1969; ALS

C6H7N+ + Benzene, hexamethyl- = (C6H7N+ • Benzene, hexamethyl-)

By formula: C6H7N+ + C12H18 = (C6H7N+ • C12H18)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr17.1kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr24.3cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Anti-1,2,3,5,6-pentamethyl-4-methylenebicyclo[3.1.0]hex-2-ene = Benzene, hexamethyl-

By formula: C12H18 = C12H18

Quantity Value Units Method Reference Comment
Δr-42.7kcal/molCisoChilds and Mulholland, 1983liquid phase; ALS

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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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

Spectrum

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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 223
NIST MS number 228195

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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, J. Phys. Chem., 1957, 61, 730-735. [all data]

Oth, 1968
Oth, J.F.M., The kinetics and thermochemistry of the thermal rearrangement of hexamethylbicyclo[2.2.0]hexa-2,5-diene (hexamethyldewarbenzene) and of hexamethyltetracyclo[2.2.0,0(2,6).0(3,5)]hexane (hexamethylprismane), Chem. Ber., 1968, 47, 1185-1195. [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]

Holdiness, 1984
Holdiness, M.R., Resonance energy of hexaethylbenzene and hexamethylbenzene, Thermochim. Acta, 1984, 78, 435-436. [all data]

Atake, Gyoten, et al., 1982
Atake, T.; Gyoten, H.; Chihara, H., A concealed anomaly at 117.5 K in the heat capacity of hexamethylbenzene, J. Chem. Phys., 1982, 76(11), 5535-5540. [all data]

Frankosky and Aston, 1965
Frankosky, M.; Aston, J.G., The heat capacity and entropy of hexamethylbenzene from 13 to 340 K. An estimate of the internal rotation barrier, J. Phys. Chem., 1965, 69, 3126-3132. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [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]

Momotani, Suga, et al., 1956
Momotani, M.; Suga, H.; Seki, S.; Nitta, I., Phase transitions in crystals composed of organic molecules with methyl groups at the molecular periperies, Proceed. National Academy of Sci. (India), XXV(Section A, part, 1956, II), 74-82. [all data]

Spaght, Thomas, et al., 1932
Spaght, M.E.; Thomas, S.B.; Parks, G.S., Some heat capacity data on organic compounds obtained with a radiation calorimeter, J. Phys. Chem., 1932, 36, 882-888. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Cooper, Crowne, et al., 1967
Cooper, A.R.; Crowne, C.W.P.; Farrell, P.G., Gas-Liquid Chromatographic Studies of Electron-Donor-Acceptor Systems, Trans. Faraday Soc., 1967, 63, 447. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R., The Critical Temperatures and Pressures of Thirty Organic Compounds, J. Appl. Chem. Biotechnol., 1974, 24, 359. [all data]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]

Zhao, Unhannanant, et al., 2008
Zhao, Hui; Unhannanant, Patamaporn; Hanshaw, William; Chickos, James S., Enthalpies of Vaporization and Vapor Pressures of Some Deuterated Hydrocarbons. Liquid-Vapor Pressure Isotope Effects, J. Chem. Eng. Data, 2008, 53, 7, 1545-1556, https://doi.org/10.1021/je800091s . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Ambrose, Lawrenson, et al., 1976
Ambrose, D.; Lawrenson, I.J.; Sprake, C.H.S., The vapour pressure of hexamethylbenzene, The Journal of Chemical Thermodynamics, 1976, 8, 5, 503-504, https://doi.org/10.1016/0021-9614(76)90071-9 . [all data]

Overberger, Steele, et al., 1969
Overberger, John E.; Steele, William A.; Aston, John G., The vapor pressure of hexamethylbenzene the standard entropy of hexamethylbenzene vapor and the barrier to internal rotation, The Journal of Chemical Thermodynamics, 1969, 1, 6, 535-542, https://doi.org/10.1016/0021-9614(69)90014-7 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Spaght, Thomas, et al., 1931
Spaght, M.E.; Thomas, S.B.; Parks, G.S., Some Heat-Capacity Data on Organic Compounds obtained with a Radiation Calorimeter, J. Phys. Chem., 1931, 36, 3, 882-888, https://doi.org/10.1021/j150333a009 . [all data]

Fujiwara, Inaba, et al., 1992
Fujiwara, T.; Inaba, A.; Atake, T.; Chihara, H., Thermodynamic properties of deuterated hexamethylbenzene and of its solid solutions with the hydrogenated analog. A large isotope effect on the phase transition at the temperature 117 K, J. Chem. Thermodynam., 1992, 24, 863-881. [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Yoshimoto, Fujiwara, et al., 1985
Yoshimoto, Y.; Fujiwara, T.; Atake, T.; Chihara, H., Solid-solid transition in hexamethylbenzene that depends on thermal history, Chem. Lett., 1985, (9), 1347-1350. [all data]

Adam and Chang, 1969
Adam, W.; Chang, J.C., Kinetics and thermochemistry of valence isomerization by differential scanning calorimetry: the case of hexamethylprismane and hexamethyldewarbenzene, Int. J. Chem. Kinet., 1969, 1, 487-492. [all data]

Oth, 1969
Oth, J.F.M., The kinetics and thermochemistry of the thermal rearrangement of hexamethyl(Dewar benzene) and of hexamethylprismane, Angew. Chem. Int. Ed. Engl., 1969, 7, 646. [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Childs and Mulholland, 1983
Childs, R.F.; Mulholland, D.L., Thermochemical relationships between some bicyclohexenyl and benzenium cations, J. Am. Chem. Soc., 1983, 105, 96-99. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References