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Cyclopentane

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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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

Hydrogen + Cyclopentene = Cyclopentane

By formula: H2 + C5H8 = C5H10

Quantity Value Units Method Reference Comment
Deltar-26.94 ± 0.13kcal/molChydAllinger, Dodziuk, et al., 1982liquid phase; solvent: Hexane; ALS
Deltar-26.8 ± 0.2kcal/molChydRoth and Lennartz, 1980liquid phase; solvent: Cyclohexane; ALS
Deltar-26.04 ± 0.44kcal/molChydTurner, Jarrett, et al., 1973liquid phase; solvent: Acetic acid; ALS
Deltar-26.2 ± 0.2kcal/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS
Deltar-26.67 ± 0.06kcal/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -26.92 ± 0.06 kcal/mol; At 355 °K; ALS

C5H9- + Hydrogen cation = Cyclopentane

By formula: C5H9- + H+ = C5H10

Quantity Value Units Method Reference Comment
Deltar416.1 ± 2.0kcal/molBranDePuy, Gronert, et al., 1989gas phase; B
Deltar418.3 ± 2.0kcal/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Deltar407.4 ± 2.1kcal/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Deltar409.6 ± 2.1kcal/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

Hydrogen + Bicyclo[2.1.0]pentane = Cyclopentane

By formula: H2 + C5H8 = C5H10

Quantity Value Units Method Reference Comment
Deltar-56.1 ± 0.1kcal/molChydRoth, Klarner, et al., 1980liquid phase; solvent: Heptane; ALS
Deltar-55.14 ± 0.36kcal/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid; ALS

2Hydrogen + 1,3-Cyclopentadiene = Cyclopentane

By formula: 2H2 + C5H6 = C5H10

Quantity Value Units Method Reference Comment
Deltar-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

2Hydrogen + Bicyclo[2.1.0]pent-2-ene = Cyclopentane

By formula: 2H2 + C5H6 = C5H10

Quantity Value Units Method Reference Comment
Deltar-98.0 ± 0.5kcal/molChydRoth, Klarner, et al., 1980liquid phase; solvent: Heptane; ALS

Cyclopentane + Iodine = 2Hydrogen iodide + Cyclopentene

By formula: C5H10 + I2 = 2HI + C5H8

Quantity Value Units Method Reference Comment
Deltar24.40kcal/molEqkFuruyama, Golden, et al., 1970gas 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.

Allinger, Dodziuk, et al., 1982
Allinger, N.L.; Dodziuk, H.; Rogers, D.W.; Naik, S.N., Heats of hydrogenation and formation of some 5-membered ring compounds by molecular mechanics calculations and direct measurements, Tetrahedron, 1982, 38, 1593-1597. [all data]

Roth and Lennartz, 1980
Roth, W.R.; Lennartz, H.W., Heats of hydrogenation. I. Determination of heats of hydrogenation with an isothermal titration calorimeter, Chem. Ber., 1980, 113, 1806-1817. [all data]

Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J., Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins, J. Am. Chem. Soc., 1973, 95, 790-792. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [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]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [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]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [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]

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]


Notes

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