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Cyclopentanone

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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
Deltafgas-197.4 ± 1.3kJ/molCmWiberg, Crocker, et al., 1991ALS
Deltafgas-194.8 ± 1.7kJ/molCcbWolf, 1972ALS
Deltafgas-193.0 ± 1.8kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -193.8 kJ/mol; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
38.3150.Thermodynamics Research Center, 1997p=1 bar. Selected entropies and heat capacities agree within 2 J/mol*K with statistical values calculated by [ Shvaro O.V., 1987] except for S(1000 K) which value is about 6 J/mol*K lower than that of [ Thermodynamics Research Center, 1997]. Discrepancies with statistical calculation of [ Andreevskii D.N., 1976] amount to 4-12 J/mol*K for S(T) and 3-8 J/mol*K for Cp(T).; GT
45.17100.
53.92150.
65.64200.
87.22273.15
95.33298.15
95.93300.
128.42400.
157.31500.
181.43600.
201.42700.
218.14800.
232.24900.
244.211000.
254.411100.
263.11200.
270.61300.
277.11400.
282.61500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
116.90360.Shvaro O.V., 1987GT
121.16375.
128.03400.
133.86420.
139.31440.
144.04460.
149.22480.

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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-240.2 ± 1.3kJ/molCmWiberg, Crocker, et al., 1991 
Deltafliquid-237.4 ± 1.7kJ/molCcbWolf, 1972 
Deltafliquid-236.5kJ/molCcbSellers and Sunner, 1962 
Quantity Value Units Method Reference Comment
Deltacliquid-2873.5 ± 1.6kJ/molCcbWolf, 1972Corresponding «DELTA»fliquid = -237.35 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2874.0 ± 0.92kJ/molCcbSellers and Sunner, 1962Corresponding «DELTA»fliquid = -236.9 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2870. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding «DELTA»fliquid = -241. kJ/mol (simple calculation by NIST; no Washburn corrections)

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
Deltar-60.25 ± 0.67kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Deltar-51.25 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -52.3 ± 0.3 kJ/mol; At 355 K; ALS

C5H7O- + Hydrogen cation = Cyclopentanone

By formula: C5H7O- + H+ = C5H8O

Quantity Value Units Method Reference Comment
Deltar1540. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1507. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; B

Cyclopentanol = Cyclopentanone + Hydrogen

By formula: C5H10O = C5H8O + H2

Quantity Value Units Method Reference Comment
Deltar54.9 ± 4.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS
Deltar51.30kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

1-Methoxycyclopentene + Water = Cyclopentanone + Methyl Alcohol

By formula: C6H10O + H2O = C5H8O + CH4O

Quantity Value Units Method Reference Comment
Deltar-21.22 ± 0.69kJ/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
Deltar16. ± 2.kJ/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
Deltar-44. ± 1.kJ/molCmWiberg, Morgan, et al., 1994gas phase; ALS

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

Quantity Value Units Method Reference Comment
Deltar-11.6 ± 1.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas 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.

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]

Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Sellers and Sunner, 1962
Sellers, P.; Sunner, S., Heats of combustion of cyclic ketones and alcohols, Acta Chem. Scand., 1962, 16, 46-52. [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]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Shvaro O.V., 1987
Shvaro O.V., Thermodynamic properties of cyclopentanone and cyclohexanone, Inzh.-Fiz. Zh., 1987, 52, 807-812. [all data]

Andreevskii D.N., 1976
Andreevskii D.N., Thermodynamic properties of C4-C6 cyclic ketones, Zh. Prikl. Khim., 1976, 49, 1819-1823. [all data]

Skuratov, Kozina, et al., 1957
Skuratov, S.M.; Kozina, M.L.; Shteher, S.M.; Varushyenko, R.M., The heats of combustion of several purified compounds, Thermochem. Bull. (Moscow State Univ.), March, 1957, 36-37. [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]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References