Cyclopentanone

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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

Cyclopentanone + Hydrogen = Cyclopentanol

By formula: C5H8O + H2 = C5H10O

Quantity Value Units Method Reference Comment
Δr-14.40 ± 0.16kcal/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-12.25 ± 0.15kcal/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -12.50 ± 0.06 kcal/mol; At 355 K; ALS

C5H7O- + Hydrogen cation = Cyclopentanone

By formula: C5H7O- + H+ = C5H8O

Quantity Value Units Method Reference Comment
Δr368.0 ± 4.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr360.3 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; B

Cyclopentanol = Cyclopentanone + Hydrogen

By formula: C5H10O = C5H8O + H2

Quantity Value Units Method Reference Comment
Δr13.1 ± 1.1kcal/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS
Δr12.26kcal/molEqkCubberley and Mueller, 1946gas phase; ALS

1-Methoxycyclopentene + Water = Cyclopentanone + Methyl Alcohol

By formula: C6H10O + H2O = C5H8O + CH4O

Quantity Value Units Method Reference Comment
Δr-5.07 ± 0.17kcal/molCmHine and Arata, 1976liquid phase; Heat of hydrolysis; ALS

Water + 1,1-Dimethoxycyclopentane = Cyclopentanone + 2Methyl Alcohol

By formula: H2O + C7H14O2 = C5H8O + 2CH4O

Quantity Value Units Method Reference Comment
Δr3.9 ± 0.4kcal/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

Cyclopentanone + 2Methyl Alcohol = Water + 1,1-Dimethoxycyclopentane

By formula: C5H8O + 2CH4O = H2O + C7H14O2

Quantity Value Units Method Reference Comment
Δr-10.4 ± 0.3kcal/molCmWiberg, Morgan, et al., 1994gas phase; ALS

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

Quantity Value Units Method Reference Comment
Δr-2.77 ± 0.41kcal/molEqkFedoseenko, Yursha, et al., 1984gas 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.

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system, Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]

Hine and Arata, 1976
Hine, J.; Arata, K., Keto-Enol tautomerism. I. The calorimetrical determination of the equilibrium constant for keto-enol tautomerism for cyclopentanone and acetone, Bull. Chem. Soc. Jpn., 1976, 49, 3085-3088. [all data]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]


Notes

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