1,3-Cyclopentadiene

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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

Quantity Value Units Method Reference Comment
Δfgas33.2kcal/molChydRoth, Adamczak, et al., 1991ALS
Δfgas31.89kcal/molEqkFuruyama, Golden, et al., 1970ALS
Quantity Value Units Method Reference Comment
Δcgas-707. ± 7.kcal/molCcbWassermann, 1935Corresponding Δfgas = 32. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
gas65.600cal/mol*KN/AFuruyama S., 1970This a second law entropy value was obtained from study of gas-phase equilibrium. The value of S(298.2 K)=270.3(4.2) J/mol*K was obtained from other equilibrium study [ Grant C.J., 1969].; GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
7.95750.Dorofeeva O.V., 1986Recommended S(T) values differ from other statistically calculated values [ Turnbull A.G., 1967, Furuyama S., 1970] up to 2.6 J/mol*K. Discrepancies in Cp(T) values amount to 1.3-4.3 J/mol*K. There is an excellent agreement between selected values of S(T) and Cp(T) and those obtained by ab initio calculation [ Karni M., 1991].; GT
8.375100.
9.637150.
11.84200.
16.32273.15
18.01 ± 0.48298.15
18.14300.
24.689400.
30.222500.
34.663600.
38.250700.
41.207800.
43.683900.
45.7821000.
47.5721100.
49.1091200.
50.4301300.
51.5701400.
52.5621500.

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 by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
liquid43.67cal/mol*KN/ALebedev and Lityagov, 1977 

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
27.56298.15Lebedev and Lityagov, 1977T = 14 to 330 K.

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

Quantity Value Units Method Reference Comment
Tboil314. ± 2.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus183.15KN/AMurphy and Duggan, 1949Uncertainty assigned by TRC = 10. K; TRC
Tfus188.KN/AStaudinger, 1926Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Ttriple176.60KN/ALebedev and Lityagov, 1977, 2Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Δvap6.9kcal/molVRogers, 1972ALS
Δvap6.78 ± 0.06kcal/molVHull, Reid, et al., 1965ALS
Δvap6.79 ± 0.07kcal/molMMHull, Reid, et al., 1965, 2Based on data from 291. to 314. K.; AC
Δvap7.10kcal/molN/AHull, Reid, et al., 1965, 2Based on data from 273. to 287. K. See also Barrett and Burrage, 1932.; AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
6.72302.A,MMStephenson and Malanowski, 1987Based on data from 291. to 314. K. See also Hull, Reid, et al., 1965, 2.; AC
6.74286.N/ALesteva, Ogorodnikov, et al., 1967Based on data from 271. to 314. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
271.3 to 314.2.64802531.826-113.863Lesteva, Ogoradnikov, et al., 1967Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.914176.60Lebedev and Lityagov, 1977DH
1.91176.6Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
10.9176.60Lebedev and Lityagov, 1977DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Δr353.9 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr354.9 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Δr357.2 ± 2.0kcal/molD-EAEngelking and Lineberger, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr347.7 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr348.7 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

cyclopentadienide anion + 1,3-Cyclopentadiene = (cyclopentadienide anion • 1,3-Cyclopentadiene)

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

Quantity Value Units Method Reference Comment
Δr<8.60kcal/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr20.cal/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M
Quantity Value Units Method Reference Comment
Δr<2.6 ± 1.0kcal/molIMRBMeot-ner, 1988gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
3.6250.PHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M

Maleic anhydride + 1,3-Cyclopentadiene = Carbic anhydride

By formula: C4H2O3 + C5H6 = C9H8O3

Quantity Value Units Method Reference Comment
Δr-24.8 ± 0.5kcal/molCmBreslauer and Kabakoff, 1974liquid phase; solvent: Dioxane; ALS
Δr-25.78kcal/molCmRogers and Quan, 1973liquid phase; Gas phase Diels-Alder; ALS

2Hydrogen + 1,3-Cyclopentadiene = Cyclopentane

By formula: 2H2 + C5H6 = C5H10

Quantity Value Units Method Reference Comment
Δr-50.38 ± 0.20kcal/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -50.87 ± 0.20 kcal/mol; At 355 °K; ALS

Chlorine anion + 1,3-Cyclopentadiene = (Chlorine anion • 1,3-Cyclopentadiene)

By formula: Cl- + C5H6 = (Cl- • C5H6)

Quantity Value Units Method Reference Comment
Δr<2.50kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
2.5300.PHPMSFrench, Ikuta, et al., 1982gas phase; DG<; M

1,3-Cyclopentadiene + Tetracyanoethylene = Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile

By formula: C5H6 + C6N4 = C11H6N4

Quantity Value Units Method Reference Comment
Δr-26.8kcal/molKinSamuilov, Bukharov, et al., 1981liquid phase; solvent: Chorobenzene; ALS
Δr-25.56 ± 0.70kcal/molCmRogers, 1972liquid phase; ALS

2,5-Norbornadiene = 1,3-Cyclopentadiene + Acetylene

By formula: C7H8 = C5H6 + C2H2

Quantity Value Units Method Reference Comment
Δr28.00 ± 0.50kcal/molKinWalsh and Wells, 1975gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 28.36 ± 0.32 kcal/mol; ALS

21,3-Cyclopentadiene (l) + magnesium (cr) = Magnesium, bis(η(5)-2,4-cyclopentadien-1-yl)- (cr) + Hydrogen (g)

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

Quantity Value Units Method Reference Comment
Δr-34.06 ± 0.69kcal/molRSCHull, Reid, et al., 1967Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS

C8H6MoO3 (solution) + 31,3-Diazine (solution) = C18H15MoN3O3 (solution) + 1,3-Cyclopentadiene (solution)

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

Quantity Value Units Method Reference Comment
Δr-16.7 ± 0.69kcal/molRSCNolan, Hoff, et al., 1985solvent: Pyridine; Reaction temperature: 323 K; MS

Bicyclo[2.1.0]pent-2-ene = 1,3-Cyclopentadiene

By formula: C5H6 = C5H6

Quantity Value Units Method Reference Comment
Δr-47.8 ± 0.5kcal/molCisoRoth, Klarner, et al., 1980liquid phase; solvent: Heptane; ALS

Dicyclopentadiene = 21,3-Cyclopentadiene

By formula: C10H12 = 2C5H6

Quantity Value Units Method Reference Comment
Δr17.300kcal/molCmBaur and Frater, 1941gas phase; Heat of dissociation; ALS

2Hydrogen iodide + 1,3-Cyclopentadiene = Cyclopentene + Iodine

By formula: 2HI + C5H6 = C5H8 + I2

Quantity Value Units Method Reference Comment
Δr-21.4kcal/molEqkFuruyama, Golden, et al., 1970gas phase; ALS

2-Norbornene = 1,3-Cyclopentadiene + Ethylene

By formula: C7H10 = C5H6 + C2H4

Quantity Value Units Method Reference Comment
Δr23.2 ± 0.60kcal/molEqkWalsh and Wells, 1976gas phase; ALS

Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclopentadiene + Tetracyanoethylene

By formula: C11H6N4 = C5H6 + C6N4

Quantity Value Units Method Reference Comment
Δr25.56 ± 0.70kcal/molCmRogers, 1972solid phase; ALS

1,3-Cyclopentadiene + Acetylene = 2,5-Norbornadiene

By formula: C5H6 + C2H2 = C7H8

Quantity Value Units Method Reference Comment
Δr-28.0 ± 0.5kcal/molEqkWalsh and Wells, 1975gas phase; ALS

21,3-Cyclopentadiene = endo-Dicyclopentadiene

By formula: 2C5H6 = C10H12

Quantity Value Units Method Reference Comment
Δr-46.62kcal/molEqkLenz and Vaughan, 1989gas phase; ALS

21,3-Cyclopentadiene = C10H12

By formula: 2C5H6 = C10H12

Quantity Value Units Method Reference Comment
Δr-46.77kcal/molEqkLenz and Vaughan, 1989gas phase; ALS

References

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

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

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

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