1,3-Cyclopentadiene

• Formula: C₅H₆
• Molecular weight: 66.1011
• IUPAC Standard InChI: InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2 Copy

  
• IUPAC Standard InChIKey: ZSWFCLXCOIISFI-UHFFFAOYSA-N Copy
• CAS Registry Number: 542-92-7
• 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: Cyclopentadiene; Pentole; Pyropentylene; R-Pentine
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

Constant pressure heat capacity of gas

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
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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Kovats' RI, polar column, isothermal

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Kovats' RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521. [all data]

Furuyama, Golden, et al., 1970
Furuyama, S.; Golden, D.M.; Benson, S.W., Thermochemistry of cyclopentene and cyclopentadiene from studies of gas-phase equilibria, J. Chem. Thermodyn., 1970, 2, 161-169. [all data]

Wassermann, 1935
Wassermann, A., The mechanism of additions to double bonds. Part I. Thermochemistry and kinetics of a diene synthesis, J. Chem. Soc., 1935, 828-838. [all data]

Furuyama S., 1970
Furuyama S., Thermochemistry of cyclopentene and cyclopentadiene from studies of gas-phase equilibria, J. Chem. Thermodyn., 1970, 2, 161-169. [all data]

Grant C.J., 1969
Grant C.J., Reversibility in the gas-phase decomposition of cyclopentene. The entropy of cyclopentadiene, J. Chem. Soc. Chem. Comm., 1969, 667-668. [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]

Turnbull A.G., 1967
Turnbull A.G., Thermochemistry of biscyclopentadienyl metal compounds, Austral. J. Chem., 1967, 20, 2059-2067. [all data]

Karni M., 1991
Karni M., Ab initio calculations and ideal gas thermodynamic functions of cyclopentadiene and cyclopentadiene derivatives, J. Phys. Chem. Ref. Data, 1991, 20, 665-683. [all data]

Murphy and Duggan, 1949
Murphy, M.T.; Duggan, A.C., Pyrolysis of Butadiene, J. Am. Chem. Soc., 1949, 71, 3347. [all data]

Staudinger, 1926
Staudinger, H., Ber. Dtsch. Chem. Ges., 1926, 59, 3019. [all data]

Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya., Thermodynamics of polypentenamer synthesis reactions crystalline polytetrahydrofuran at 0 K, Vysokomol. Soedin., Ser. B, 1977, 19, 558. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [all data]

Hull, Reid, et al., 1965
Hull, H.S.; Reid, A.F.; Turnbull, A.G., Vapour pressures of cyclopentadiene and bis(cyclopentadienyl)magnesium, Aust. J. Chem., 1965, 18, 249. [all data]

Hull, Reid, et al., 1965, 2
Hull, HS; Reid, AF; Turnbull, AG, Vapour pressures of cyclopentadiene and Bis(cyclopentadienyl)magnesium, Aust. J. Chem., 1965, 18, 2, 249-621, https://doi.org/10.1071/CH9650249 . [all data]

Barrett and Burrage, 1932
Barrett, E.G.V.; Burrage, L.J., Some Observations on the Transformation of Cyclopentadiene into its Dimeride., J. Phys. Chem., 1932, 37, 8, 1029-1035, https://doi.org/10.1021/j150350a007 . [all data]

Stephenson and Malanowski, 1987
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Lesteva, Ogorodnikov, et al., 1967
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Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Lesteva, Ogoradnikov, et al., 1967
Lesteva, T.M.; Ogoradnikov, S.K.; Morozova, A., Kinetics of Dimerisation of Cyclopentadiene and Equilibrium of Liquid-Steam in System of Isoprene-Cyclopentadiene, Zh. Prikl. Khim. (Leningrad), 1967, 40, 891-894. [all data]

Lebedev and Lityagov, 1977, 2
Lebedev, B.V.; Lityagov, V.Ya., Thermodynamics of polypentenamer synthesis reactions, Vysokomol. Soedin., 1977, B19, 558-560. [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]

Powell and Edson, 1948
Powell, J.S.; Edson, K.C., Anal. Chem., 1948, 20, 510. [all data]

Diez, Guillen, et al., 1990
Diez, M.A.; Guillen, M.D.; Blanco, C.G.; Bermejo, J., Chromatographic study of methylcyclopentadiene dimers and iso-dimers and determination of their boiling points, J. Chromatogr., 1990, 508, 363-374, https://doi.org/10.1016/S0021-9673(00)91279-2 . [all data]

Safina, Poznyak, et al., 1989
Safina, L.R.; Poznyak, T.I.; Lisitsyn, D.M.; Kiseleva, E.V.; Kovalev, G.I., Selective gas-chromatographic determination of trace unsaturated and aromatic-hydrocarbons in complex-mixtures, J. Appl. Chem. USSR (Engl. Transl.), 1989, 44, 5, 749-754. [all data]

Papazova, Milina, et al., 1988
Papazova, D.; Milina, R.; Dimov, N., Comparative evaluation of retention of hydrocarbons present in the C₅-petroleum fraction of methylsilicone and squalane phases, Chromatographia, 1988, 25, 3, 177-180, https://doi.org/10.1007/BF02316441 . [all data]

Bermejo, Blanco, et al., 1987
Bermejo, J.; Blanco, C.G.; Diez, M.A.; Guillén, M.D., Kováts retention indices of selected mono and polycyclic olefins, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1987, 10, 8, 461-463, https://doi.org/10.1002/jhrc.1240100809 . [all data]

Sojak, Ruman, et al., 1987
Sojak, L.; Ruman, J.; Janak, J., Characterization of Monoalkylcyclopentadiens by Retention-Structure Correlation in Capillary Gas Chromatography, J. Chromatogr., 1987, 391, 79-87, https://doi.org/10.1016/S0021-9673(01)94306-7 . [all data]

Bredael, 1982
Bredael, P., Retention indices of hydrocarbons on SE-30, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610 . [all data]

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Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Bajus, Veselý, et al., 1979, 2
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 1. Pyrolysis of heptane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 1, 30-37, https://doi.org/10.1021/i360069a007 . [all data]

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Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

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

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