Bicyclo[2.2.2]octane

• Formula: C₈H₁₄
• Molecular weight: 110.1968
• IUPAC Standard InChI: InChI=1S/C8H14/c1-2-8-5-3-7(1)4-6-8/h7-8H,1-6H2 Copy

  
• IUPAC Standard InChIKey: GPRLTFBKWDERLU-UHFFFAOYSA-N Copy
• CAS Registry Number: 280-33-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  View 3d structure (requires JavaScript / HTML 5)
• Other names: Cyclohexane, 1,4-endo-(1,2-ethanediyl)-; 1,4-Endoethylenecyclohexane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Phase change data

Go To: Top, Reaction 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:
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

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

Go To: Top, Phase change 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 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

2 +  =

By formula: 2H₂ + C₈H₁₀ = C₈H₁₄

 +  =

By formula: H₂ + C₈H₁₂ = C₈H₁₄

3 +  =

By formula: 3H₂ + C₈H₈ = C₈H₁₄

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

References

Go To: Top, Phase change data, Reaction 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.

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

Wong and Westrum, 1970
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]

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]

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

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]

Wong and Westrum, 1970, 2
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]

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]

Raymonda, 1972
Raymonda, J.W., Rydberg states in cyclic alkanes, J. Chem. Phys., 1972, 56, 3912. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method, J. Am. Chem. Soc., 1970, 92, 19. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.