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
ΔfH°gas33.2kcal/molChydRoth, Adamczak, et al., 1991ALS
ΔfH°gas31.89kcal/molEqkFuruyama, Golden, et al., 1970ALS
Quantity Value Units Method Reference Comment
ΔcH°gas-707. ± 7.kcal/molCcbWassermann, 1935Corresponding ΔfHºgas = 32. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
S°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
S°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.

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

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Individual Reactions

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
ΔrH°353.9 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
ΔrH°354.9 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
ΔrH°357.2 ± 2.0kcal/molD-EAEngelking and Lineberger, 1977gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°347.7 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
ΔrG°348.7 ± 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
ΔrH°<8.60kcal/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
ΔrS°20.cal/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, ΔrH<; M
Quantity Value Units Method Reference Comment
ΔrG°<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
ΔrH°-24.8 ± 0.5kcal/molCmBreslauer and Kabakoff, 1974liquid phase; solvent: Dioxane; ALS
ΔrH°-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
ΔrH°-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
ΔrG°<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
ΔrH°-26.8kcal/molKinSamuilov, Bukharov, et al., 1981liquid phase; solvent: Chorobenzene; ALS
ΔrH°-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
ΔrH°28.00 ± 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
ΔrH°-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
ΔrH°-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
ΔrH°-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
ΔrH°17.300kcal/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
ΔrH°-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
ΔrH°23.2 ± 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
ΔrH°25.56 ± 0.70kcal/molCmRogers, 1972solid phase; ALS

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

By formula: C5H6 + C2H2 = C7H8

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

21,3-Cyclopentadiene = C10H12

By formula: 2C5H6 = C10H12

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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]

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]

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]

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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