Cyclooctane

• Formula: C₈H₁₆
• Molecular weight: 112.2126
• IUPAC Standard InChI: InChI=1S/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2 Copy

  
• IUPAC Standard InChIKey: WJTCGQSWYFHTAC-UHFFFAOYSA-N Copy
• CAS Registry Number: 292-64-8
• 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.
• Other names: Octamethylene
• 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
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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:
DRB - Donald R. Burgess, Jr.
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

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

 +  =

By formula: H₂ + C₈H₁₄ = C₈H₁₆

 +  =

By formula: H₂ + C₈H₁₄ = C₈H₁₆

3 +  =

By formula: 3H₂ + C₈H₁₀ = C₈H₁₆

2 +  =

By formula: 2H₂ + C₈H₁₂ = C₈H₁₆

 + 2 =

By formula: C₈H₁₂ + 2H₂ = C₈H₁₆

2 +  =

By formula: 2H₂ + C₈H₁₂ = C₈H₁₆

 + 2 =

By formula: C₈H₁₂ + 2H₂ = C₈H₁₆

3 +  =

By formula: 3H₂ + C₈H₁₀ = C₈H₁₆

4 +  =

By formula: 4H₂ + C₈H₈ = C₈H₁₆

4 +  =

By formula: 4H₂ + C₈H₈ = C₈H₁₆

 +  =

By formula: H₂ + C₈H₁₄ = C₈H₁₆

2 +  =

By formula: 2H₂ + C₈H₁₂ = C₈H₁₆

2 +  =

By formula: 2H₂ + C₈H₁₂ = C₈H₁₆

2 +  =

By formula: 2H₂ + C₈H₁₂ = C₈H₁₆

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 4000-1330, 10% CS2 FOR 1330-450 CM^-1) VS SOLVENT; CARY 90 (GRATING); 2 cm^-1 resolution

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

• gas

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics 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.

Spitzer and Huffman, 1947
Spitzer, R.; Huffman, H.M., The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane, J. Am. Chem. Soc., 1947, 69, 211-213. [all data]

Finke H.L., 1956
Finke H.L., Cycloheptane, cyclooctane, and 1,3,5-cycloheptatriene. Low-temperature thermal properties, vapor pressure, and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [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]

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Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Chang S., 1970
Chang S., The heats of combustion and strain energies of bicyclo[n.m.0]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [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]

Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J., Thermal quantities of some cycloparaffins. Part III. Results of measurements, Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]

Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-5476. [all data]

Ruzieka and Schlapfer, 1933
Ruzieka, L.; Schlapfer, P., Zur kenntnis des kohlenstoffringes XXII. Uber die verbrennungswarme bei hochgliedrigen ringverbindungen, Helv. Chim. Acta, 1933, 16, 162-169. [all data]

Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]

Tanaka, 1985
Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269. [all data]

Fortier, D'Arcy, et al., 1979
Fortier, J.-L.; D'Arcy, P.J.; Benson, G.C., Heat capacities of binary cycloalkane mixtures at 298.15 K, Thermochim. Acta, 1979, 28, 37-43. [all data]

Wilhelm, Faradjzadeh, et al., 1979
Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E., Molar excess heat capacities and excess volumes of 1,2-dichloroethane + cyclooctane, + mesitylene, and + tetrachloromethane, J. Chem. Thermodynam., 1979, 11, 979-984. [all data]

Jolicoeur, Boileau, et al., 1975
Jolicoeur, C.; Boileau, J.; Bazinet, S.; Picker, P., Thermodynamic properties of aqueous organic solutes in relation to their structure. Part II. Apparent molal volumes and heat capacities of c-alkylamine hydrobromides in water, Can. J. Chem., 1975, 53, 716-722. [all data]

Finke, Scott, et al., 1956, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, Cyclooctane and 1,3,5-Cycloheptatriene. Low Temperature Thermal Properties, Vapor Pressure and Derived Chemical Thermodynamic Prop., J. Am. Chem. Soc., 1956, 78, 5469. [all data]

Waddington, 1955
Waddington, G., Personal Commun., 1955. [all data]

Kaarsemaker, 1951
Kaarsemaker, S., , Thesis, 1951. [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372. [all data]

Young, 1972
Young, C.L., Gas-liquid critical properties of the cycloalkanes and their mixtures, Aust. J. Chem., 1972, 25, 1625-30. [all data]

Hicks and Young, 1971
Hicks, C.P.; Young, C.L., Critical Temperatures of Mixtures of Quasi-spherical Molecules. Alicyclic Hydrocarbons + Benzene, + Hexafluorobenzene and + Perfluorocyclohexane, Trans. Faraday Soc., 1971, 67, 1605-11. [all data]

Finke, Scott, et al., 1956, 3
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G., Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties, J. Am. Chem. Soc., 1956, 78, 5469-54. [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]

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]

Wu, Locke, et al., 1991
Wu, Huey S.; Locke, William E.; Sandler, Stanley I., Isothermal vapor-liquid equilibrium of binary mixtures containing morpholine, J. Chem. Eng. Data, 1991, 36, 1, 127-130, https://doi.org/10.1021/je00001a037 . [all data]

Stephenson and Malanowski, 1987
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Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Anand, Grolier, et al., 1975
Anand, Subhash C.; Grolier, Jean P.E.; Kiyohara, Osamu; Halpin, Carl J.; Benson, George C., Thermodynamic properties of some cycloalkane-cycloalkanol systems at 298. 15K. III, J. Chem. Eng. Data, 1975, 20, 2, 184-189, https://doi.org/10.1021/je60065a020 . [all data]

Bondi, 1963
Bondi, A., Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments., J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027 . [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]

Doering, Roth, et al., 1989
Doering, W.E.; Roth, W.R.; Bauer, F.; Breuckmann, R.; Ebbrecht, T.; Herbold, M.; Schmidt, R.; Lennartz, H-W.; Lenoir, D.; Boese, R., Rotational barriers of strained olefines, Chem. Ber., 1989, 122, 1263-1266. [all data]

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Rogers, D.W.; Von Voithenberg, H.; Allinger, N.L., Heats of hydrogenation of the cis and trans isomers of cyclooctene, J. Org. Chem., 1978, 43, 360-361. [all data]

Turner and Meador, 1957
Turner, R.B.; Meador, W.R., Heats of hydrogenation. IV. Hydrogenation of some cis- and trans-cycloolefins, J. Am. Chem. Soc., 1957, 79, 4133-4136. [all data]

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Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [all data]

Roth, Hopf, et al., 1994
Roth, W.R.; Hopf, H.; Horn, C., Propargyl-Stabilisierungsenergie, Chem. Ber., 1994, 127, 1781-1795. [all data]

Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J., Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins, J. Am. Chem. Soc., 1973, 95, 790-792. [all data]

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Sieck, L.W.; Mautner(Meot-Ner), M., Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions, J. Phys. Chem., 1982, 86, 3646. [all data]

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Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N., Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]

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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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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