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
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • 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:
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

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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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: C₅H₅^- + H⁺ = C₅H₆

 +  = ( • )

By formula: C₅H₅^- + C₅H₆ = (C₅H₅^- • C₅H₆)

Free energy of reaction

 +  =

By formula: C₄H₂O₃ + C₅H₆ = C₉H₈O₃

2 +  =

By formula: 2H₂ + C₅H₆ = C₅H₁₀

 +  = ( • )

By formula: Cl^- + C₅H₆ = (Cl^- • C₅H₆)

Free energy of reaction

 +  =

By formula: C₅H₆ + C₆N₄ = C₁₁H₆N₄

=  + 

By formula: C₇H₈ = C₅H₆ + C₂H₂

2 (l) +  (cr) =  (cr) +  (g)

By formula: 2C₅H₆ (l) + Mg (cr) = C₁₀H₁₀Mg (cr) + H₂ (g)

C₈H₆MoO₃ (solution) + 3 (solution) = C₁₈H₁₅MoN₃O₃ (solution) +  (solution)

By formula: C₈H₆MoO₃ (solution) + 3C₄H₄N₂ (solution) = C₁₈H₁₅MoN₃O₃ (solution) + C₅H₆ (solution)

=

By formula: C₅H₆ = C₅H₆

= 2

By formula: C₁₀H₁₂ = 2C₅H₆

2 +  =  + 

By formula: 2HI + C₅H₆ = C₅H₈ + I₂

=  + 

By formula: C₇H₁₀ = C₅H₆ + C₂H₄

=  + 

By formula: C₁₁H₆N₄ = C₅H₆ + C₆N₄

 +  =

By formula: C₅H₆ + C₂H₂ = C₇H₈

2 =

By formula: 2C₅H₆ = C₁₀H₁₂

2 = C₁₀H₁₂

By formula: 2C₅H₆ = C₁₀H₁₂

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, Phase change data, Reaction thermochemistry data, 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.

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
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]

Lesteva, Ogorodnikov, et al., 1967
Lesteva, T.M.; Ogorodnikov, S.K.; Morozova, A.I., Zh. Prikl. Khim. (Leningrad), 1967, 40, 4, 891. [all data]

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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Engelking and Lineberger, 1977
Engelking, P.C.; Lineberger, W.C., Laser photoelectron spectrometry of C₅H₅-: A determination of the electron affinity and Jahn-Teller coupling in cyclopentadienyl, J. Chem. Phys., 1977, 67, 1412. [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S., Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride, J. Org. Chem., 1974, 39, 721-722. [all data]

Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W., Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride, J. Phys. Chem., 1973, 77, 828-831. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. IV. Hydrogenation of some dienes and of benzene, J. Am. Chem. Soc., 1936, 58, 146-153. [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]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Samuilov, Bukharov, et al., 1981
Samuilov, Ya.D.; Bukharov, S.V.; Konovalov, A.I., Reactivity of tetraphenylcyclopentadiene and tetracyclone in the Diels-Alder reaction with cyanoethylenes, Zh. Org. Khim., 1981, 17, 2389-2393. [all data]

Walsh and Wells, 1975
Walsh, R.; Wells, J.M., The enthalpy of formation of bicyclo[2,2,1]hepta-2,5-diene. Thermodynamic functions of bicyclo[2,2,1]heptane and bicyclo[2,2,1]hepta-2,5-diene, J. Chem. Thermodyn., 1975, 7, 149-154. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Hull, Reid, et al., 1967
Hull, H.S.; Reid, A.F.; Turnbull, A.G., Inorg. Chem., 1967, 6, 805. [all data]

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

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Nolan, Hoff, et al., 1985
Nolan, S.P.; Hoff, C.D.; Landrum, J.T., J. Organometal. Chem., 1985, 282, 357. [all data]

Roth, Klarner, et al., 1980
Roth, W.R.; Klarner, F.-G.; Lennartz, H.-W., Heats of hydrogenation. II. Heat of hydrogenation of bicyclo[2.1.0]pent-2-ene, an antiaromatic system, Chem. Ber., 1980, 113, 1806-1818. [all data]

Baur and Frater, 1941
Baur, E.; Frater, S., Kinetik der bildung und des zerfalls von dicyclopentadien, Helv. Chim. Acta, 1941, 24, 768-783. [all data]

Walsh and Wells, 1976
Walsh, R.; Wells, J.M., The enthalpy of formation and thermodynamic functions of bicyclo[2,2,1]hept-2-ene, J. Chem. Thermodyn., 1976, 8, 55-60. [all data]

Lenz and Vaughan, 1989
Lenz, T.G.; Vaughan, J.D., Employing force-field calculations to predict equilibrium constants and other thermodynamic properties for the dimerization of 1,3-cyclopentadiene, J. Phys. Chem., 1989, 93, 1592-1596. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  S°gas	Entropy of gas at standard conditions
  T	Temperature
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  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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