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Bicyclo[2.2.2]octane

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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-99.04 ± 0.96kJ/molCcrWong and Westrum, 1971see also Boyd, Sanwal, et al., 1971, See Westrum and Wong, 1967; ALS
Quantity Value Units Method Reference Comment
gas324.7 ± 2.5J/mol*KN/ABoyd R.H., 1971GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
81.92200.Boyd R.H., 1971Selected values were obtained by force field calculation. One can expect the uncertainty in S(500 K) and Cp(T) values to be about 10 J/mol*K if compare with the authors' results for bicyclo[2.2.1]heptane.; GT
129.62298.15
130.58300.
183.05400.
231.25500.

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
Deltafsolid-147.1 ± 0.84kJ/molCcrWong and Westrum, 1971see also Boyd, Sanwal, et al., 1971, See Westrum and Wong, 1967; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-5001.93 ± 0.88kJ/molCcrWong and Westrum, 1971see also Boyd, Sanwal, et al., 1971, See Westrum and Wong, 1967; Corresponding «DELTA»fsolid = -146.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar209.95J/mol*KN/AWong and Westrum, 1970crystaline, I phase; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
157.69298.15Wong and Westrum, 1970crystaline, I phase; T = 5 to 470 K.; 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus443.KN/AWalborsky and Loncrini, 1954Uncertainty assigned by TRC = 5. K; TRC
Quantity Value Units Method Reference Comment
Ttriple447.48KN/AWong and Westrum, 1970, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltasub47.7 ± 0.8kJ/molN/ABoyd, Sanwal, et al., 1971See also Pedley and Rylance, 1977.; AC
Deltasub48.1kJ/molN/AWong and Westrum, 1971DRB

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
46.3 ± 0.8323. - 363.BGBoyd, Sanwal, et al., 1971See also Pedley and Rylance, 1977 and Stephenson and Malanowski, 1987.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
8.37447.5Acree, 1991See also Westrum, Wong, et al., 1970.; AC

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
4.586164.25crystaline, IIcrystaline, IWong and Westrum, 1970DH
8.347447.48crystaline, IliquidWong and Westrum, 1970DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
27.87164.25crystaline, II, H and S obtained separately by graphical integration of observed Cp (or total enthalpy input) subtracting contributions from extrapolated normal Cp, H, S and T not selfcrystaline, I, consistentWong and Westrum, 1970DH
18.74447.48crystaline, I, H and S obtained separately by graphical integration of observed Cp (or total enthalpy input) subtracting contributions from extrapolated normal Cp, H, S and T not selfliquid, consistentWong and Westrum, 1970DH

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

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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

2Hydrogen + Bicyclo[2.2.2]octa-2,5-diene = Bicyclo[2.2.2]octane

By formula: 2H2 + C8H10 = C8H14

Quantity Value Units Method Reference Comment
Deltar-235.2 ± 0.42kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid

Hydrogen + Bicyclo[2.2.2]oct-2-ene = Bicyclo[2.2.2]octane

By formula: H2 + C8H12 = C8H14

Quantity Value Units Method Reference Comment
Deltar-118.2 ± 0.84kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid

3Hydrogen + Bicyclo[2.2.2]octa-2,5,7-triene = Bicyclo[2.2.2]octane

By formula: 3H2 + C8H8 = C8H14

Quantity Value Units Method Reference Comment
Deltar-392.4 ± 1.3kJ/molChydTurner, 1964liquid phase; solvent: Acetic acid

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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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Additional Data

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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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114215

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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.

Wong and Westrum, 1971
Wong, S.S.; Westrum, E.F., Jr., Enthalpies of formation of globular molecules. II. Three bicyclooctanes and two bicyclononanes, J. Am. Chem. Soc., 1971, 93, 5317-5321. [all data]

Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Westrum and Wong, 1967
Westrum, E.F., Jr.; Wong, S., Strain energies and thermal properties of globular and polynuclear aromatic molecules, AEC Rept. Coo-1149-92, Contract AT(11-1)-1149, 1967, 1-7. [all data]

Boyd R.H., 1971
Boyd R.H., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Wong and Westrum, 1970
Wong, W-K.; Westrum, E.F., Jr., Thermodynamics of globular molecules. XVII. Heat capacities and transition behavior of bicyclo[2.2.2]octane and bicyclo[2.2.2]octene, J. Phys. Chem., 1970, 74, 1303-1308. [all data]

Walborsky and Loncrini, 1954
Walborsky, H.M.; Loncrini, D.F., J. Am. Chem. Soc., 1954, 76, 5396. [all data]

Wong and Westrum, 1970, 2
Wong, W.-K.; Westrum, E.F., Thermodynamics of globular molecules. XVII. Heat capacities and transition behavior of bicyclo[2.2.2]octane and bicyclo[2.2.2]octene, J. Phys. Chem., 1970, 74, 1303-8. [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Westrum, Wong, et al., 1970
Westrum, E.F., Jr.; Wong, W-K.; Morawetz, E., Thermodynamics of globular molecules. XVIII. Heat capacities and transitional behavior of 1-azabicyclo[2.2.2]octane and 3-oxabicyclo[3.2.2]nonane. Sublimation behavior of five globular molecules, J. Phys. Chem., 1970, 74, 2542-2547. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Turner, 1964
Turner, R.B., Heat of Hydrogenation of Bicyclo[2.2.2]octa-2,5,7-triene, J. Am. Chem. Soc., 1964, 86, 3586-3587. [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