1,5-Cyclooctadiene

• Formula: C₈H₁₂
• Molecular weight: 108.1809
• IUPAC Standard InChI: InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2 Copy

  
• IUPAC Standard InChIKey: VYXHVRARDIDEHS-UHFFFAOYSA-N Copy
• CAS Registry Number: 111-78-4
• 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.
• Stereoisomers:
  • 1,5-Cyclooctadiene, (Z,Z)-
  • 1,5-Cyclooctadiene, (E,E)-
  • 1,5-Cyclooctadiene, (E,Z)-
• Other names: Cycloocta-1,5-diene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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

Constant pressure heat capacity of liquid

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.
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

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₈H₁₂⁺ (ion structure unspecified)

Ionization energy determinations

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.

Lebedev, Tsvetkova, et al., 1975
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, E.G.; Lebedev, N.K., Thermodynamic properties of cyclo-octa-1,5-diene, Russ. J. Phys. Chem. (Engl. Transl.), 1975, 49, 1265. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., Thermodynamic properties of twenty-one monocyclic hydrocarbons, J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]

Ermer O., 1976
Ermer O., Conformational interconversions of cis,cis-cyclooctadiene-1,5, J. Am. Chem. Soc., 1976, 98, 3964-3970. [all data]

Lebedev, Lebedev, et al., 1975
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, Y.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of methylenecyclobutane and 1,5-cyclooctadiene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]

Lebedev, Tsvetkova, et al., 1975, 2
Lebedev, B.V.; Tsvetkova, L.Ya.; Kiparisova, Y.G.; Lebedev, N.K., Thermodynamic properties of cycloocta-1,5-diene, Zhur. Fiz. Khim., 1975, 49, 2152. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Cope and Bailey, 1948
Cope, A.C.; Bailey, W.J., Cyclic Polyolefins II. Synthesis of Cyclooctatetraene from Chloroprene, J. Am. Chem. Soc., 1948, 70, 2305. [all data]

Ott, Goates, et al., 1974
Ott, J.B.; Goates, J.R.; Reeder, J., Solid + liquid phase equilibria and solid-compound formation in hexafluorobenzene + cyclic hydrocarbons containing one or two pi-bonds, J. Chem. Thermodyn., 1974, 6, 281-5. [all data]

Cope, Stevens, et al., 1950
Cope, A.C.; Stevens, C.L.; Hochstein, F.A., Cyclic Polyolefins V. Preparation of Bromocyclooctadiens and 1,3,5-Cyclooctatriene from 1,5-Cycloctadiene, J. Am. Chem. Soc., 1950, 72, 2510-4. [all data]

Lebedev, Lebedev, et al., 1975, 2
Lebedev, B.V.; Lebedev, N.K.; Kiparisova, E.G.; Tsvetkova, L.Ya.; Rabinovich, I.B., Thermodynamics of Methlenecyclobutane and 1,5-Cyclooctadiene in II, Thermophysique, Quatrieme Confirence International de Thermodynamique Chimique, pp 20-8, 1975. [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]

Batich, Bischof, et al., 1973
Batich, C.; Bischof, P.; Heilbronner, E., The photoelectron spectra of cyclooctatetraene and its hydrogenated derivatives, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 333. [all data]

Davidson, Jones, et al., 1969
Davidson, I.M.T.; Jones, M.; Kemmitt, R.D.W., Mass spectra and appearance potentials of some 1,5-cyclooctadiene-rhodium complexes, J.Organometal. Chem., 1969, 17, 169. [all data]

Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusS	Entropy of fusion
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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