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Bicyclo[2.2.2]oct-2-ene

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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
Deltafgas26.kJ/molKinHuybrechts, Rigaux, et al., 1980Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986; ALS
Deltafgas20.4 ± 0.79kJ/molCcrWong and Westrum, 1971See Westrum and Wong, 1967; ALS
Quantity Value Units Method Reference Comment
gas316.3J/mol*KN/ACocks A.T., 1971This value was calculated from experimental values of entropy for solid bicyclo[2.2.2]oct-2-ene and enthalpy of vaporization. Value of 323.0 J/mol*K was obtained from the study of kinetics of the addition of ethylene to 1,3-cyclohexadiene [ Huybrechts G., 1980]. Estimations by means of the group additivity are equal to 331.0 [ Huybrechts G., 1980] and 330.1 J/mol*K [ Van Mele B., 1986].; 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
Deltafsolid-23. ± 0.67kJ/molCcrWong and Westrum, 1971See Westrum and Wong, 1967; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-4839.72 ± 0.67kJ/molCcrWong and Westrum, 1971See Westrum and Wong, 1967; Corresponding «DELTA»fsolid = -23.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar210.46J/mol*KN/AWong and Westrum, 1970crystaline, I phase; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
156.73298.15Wong and Westrum, 1970crystaline, I phase; T = 5 to 500 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil401. - 407.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus384. - 385.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Ttriple389.75KN/AWong and Westrum, 1970, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltasub43.4kJ/molN/AWong and Westrum, 1971DRB

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
5.4389.8Wong and Westrum, 1970AC

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.188110.50crystaline, IIIcrystaline, IIWong and Westrum, 1970Second order transition.; DH
5.648176.47crystaline, IIcrystaline, IWong and Westrum, 1970DH
5.381389.75crystaline, IliquidWong and Westrum, 1970DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
1.33110.50crystaline, IIIcrystaline, IIWong and Westrum, 1970Second; DH
24.52176.47crystaline, 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
14.39389.75crystaline, 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

Bicyclo[2.2.2]oct-2-ene = 1,3-Cyclohexadiene + Ethylene

By formula: C8H12 = C6H8 + C2H4

Quantity Value Units Method Reference Comment
Deltar136.kJ/molKinHuybrechts, Rigaux, et al., 1980gas phase; Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986

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

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 Japan AIST/NIMC Database- Spectrum MS-IW-3669
NIST MS number 238210

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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.

Huybrechts, Rigaux, et al., 1980
Huybrechts, G.; Rigaux, D.; Vankeerberghen, J.; Van Mele, B., Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase, Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]

Van Mele, Boon, et al., 1986
Van Mele, B.; Boon, G.; Huybrechts, G., Gas-phase kinetic and thermochemical data for endo- and exo-5-monosubstituted bicyclo[2.2.2]oct-2-enes, Int. J. Chem. Kinet., 1986, 18, 537-545. [all data]

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]

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]

Cocks A.T., 1971
Cocks A.T., Thermal unimolecular decomposition of bicyclo[2.2.2]oct-2-ene, J. Chem. Soc. A, 1971, 1661-1663. [all data]

Huybrechts G., 1980
Huybrechts G., Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase, Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]

Van Mele B., 1986
Van Mele B., Gas-phase kinetic and thermodynamic data for endo- and exo-5-mono-substituted bicyclo[2.2.2]oct-2-enes, Int. J. Chem. Kinet., 1986, 18, 537-545. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]

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]


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