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1,3-Cyclopentadiene

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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 - J.E. Bartmess
M - M. M. Meot-Ner (Mautner) and S. G. Lias
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
MS - J.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
Deltar1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

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

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

Quantity Value Units Method Reference Comment
Deltar<36.0kJ/molIMRBMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/AMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M
Quantity Value Units Method Reference Comment
Deltar<11. ± 4.2kJ/molIMRBMeot-ner, 1988gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
15.250.PHPMSMeot-ner, 1988gas phase; Entropy change calculated or estimated, DG<, «DELTA»rH<; M

Maleic anhydride + 1,3-Cyclopentadiene = Carbic anhydride

By formula: C4H2O3 + C5H6 = C9H8O3

Quantity Value Units Method Reference Comment
Deltar-104. ± 2.kJ/molCmBreslauer and Kabakoff, 1974liquid phase; solvent: Dioxane; ALS
Deltar-107.9kJ/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
Deltar-210.8 ± 0.84kJ/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -212.8 ± 0.84 kJ/mol; At 355 °K; ALS

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

By formula: Cl- + C5H6 = (Cl- bullet C5H6)

Quantity Value Units Method Reference Comment
Deltar<10.5kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
10.300.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
Deltar-112.kJ/molKinSamuilov, Bukharov, et al., 1981liquid phase; solvent: Chorobenzene; ALS
Deltar-106.9 ± 2.9kJ/molCmRogers, 1972liquid phase; ALS

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

By formula: C7H8 = C5H6 + C2H2

Quantity Value Units Method Reference Comment
Deltar117.2 ± 2.1kJ/molKinWalsh and Wells, 1975gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 118.7 ± 1.3 kJ/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
Deltar-142.5 ± 2.9kJ/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
Deltar-69.9 ± 2.9kJ/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
Deltar-200. ± 2.kJ/molCisoRoth, Klarner, et al., 1980liquid phase; solvent: Heptane; ALS

Dicyclopentadiene = 21,3-Cyclopentadiene

By formula: C10H12 = 2C5H6

Quantity Value Units Method Reference Comment
Deltar72.383kJ/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
Deltar-89.5kJ/molEqkFuruyama, Golden, et al., 1970gas phase; ALS

2-Norbornene = 1,3-Cyclopentadiene + Ethylene

By formula: C7H10 = C5H6 + C2H4

Quantity Value Units Method Reference Comment
Deltar97.2 ± 2.5kJ/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
Deltar106.9 ± 2.9kJ/molCmRogers, 1972solid phase; ALS

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

By formula: C5H6 + C2H2 = C7H8

Quantity Value Units Method Reference Comment
Deltar-117. ± 2.kJ/molEqkWalsh and Wells, 1975gas phase; ALS

21,3-Cyclopentadiene = endo-Dicyclopentadiene

By formula: 2C5H6 = C10H12

Quantity Value Units Method Reference Comment
Deltar-195.1kJ/molEqkLenz and Vaughan, 1989gas phase; ALS

21,3-Cyclopentadiene = C10H12

By formula: 2C5H6 = C10H12

Quantity Value Units Method Reference Comment
Deltar-195.7kJ/molEqkLenz and Vaughan, 1989gas phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

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]

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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