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Cyclohexanone

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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-231.1 ± 0.88kJ/molCmWiberg, Crocker, et al., 1991ALS
Deltafgas-225.7kJ/molEqkKabo, Yursha, et al., 1988ALS
Deltafgas-227.7 ± 1.9kJ/molCcbWolf, 1972ALS
Deltafgas-226.3kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
gas335.53J/mol*KN/AKabo G.J., 1988GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
121.06298.15Kabo G.J., 1988Selected thermodynamic functions are in better agreement with experimental values of S(298.15 K) and Cp(T) than statistical values calculated by [ Thermodynamics Research Center, 1997, Andreevskii D.N., 1976]. Maximum discrepancies with functions given in [ Thermodynamics Research Center, 1997] amount to 2.5 and 5.0 J/mol*K for S(T) and Cp(T), respectively. Discrepancies with data [ Andreevskii D.N., 1976] reach 11 and 8 J/mol*K for S(T) and Cp(T), respectively.; GT
121.89300.
161.88400.
196.39500.
225.24600.
249.27700.
269.47800.
286.51900.
301.061000.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
155.20385.Shvaro O.V., 1987The experimental values of Cp(T) obtained by [ Vilcu R., 1975] seem to be not enough reliable in view of the comparison of experimental heat capacities of some alcohols and ketones measured by these authors (see [ Kabo G.J., 1995]).; GT
161.07400.
168.98420.
175.81440.
183.65460.
190.18480.

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-276.1 ± 0.84kJ/molCmWiberg, Crocker, et al., 1991ALS
Deltafliquid-272.6 ± 1.8kJ/molCcbWolf, 1972ALS
Deltafliquid-254. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962ALS
Deltafliquid-271.4kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3517.6 ± 1.7kJ/molCcbWolf, 1972Corresponding «DELTA»fliquid = -272.58 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3536. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962Corresponding «DELTA»fliquid = -254. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3518.9 ± 1.0kJ/molCcbSellers and Sunner, 1962Corresponding «DELTA»fliquid = -271.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3499. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding «DELTA»fliquid = -291. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid229.03J/mol*KN/ANakamura, Suga, et al., 1980DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
177.20300.Nakamura, Suga, et al., 1980T = 13 to 300 K. Unsmoothed experimental datum for Cp at 296.40 K is 175.96 J/mol*K.; DH
200.4304.2Phillip, 1939DH
177.8290.Herz and Bloch, 1924DH

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

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

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Deltar1533. ± 8.4kJ/molD-EABrinkman, Berger, et al., 1993gas phase; B
Deltar1531. ± 9.6kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Deltar1544. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Deltar1501. ± 9.6kJ/molH-TSBrinkman, Berger, et al., 1993gas phase; B
Deltar1498. ± 11.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; B
Deltar1511. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B

Cyclohexanone + Hydrogen = Cyclohexanol

By formula: C6H10O + H2 = C6H12O

Quantity Value Units Method Reference Comment
Deltar-75.86 ± 0.50kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Deltar-63.51 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -64.5 ± 0.3 kJ/mol; At 355 K; ALS

Cyclohexanol = Cyclohexanone + Hydrogen

By formula: C6H12O = C6H10O + H2

Quantity Value Units Method Reference Comment
Deltar63.4 ± 2.3kJ/molEqkKabo, Yursha, et al., 1988gas phase; Dehydrogenation; ALS

Water + Cyclohexene, 1-methoxy- = Cyclohexanone + Methyl Alcohol

By formula: H2O + C7H12O = C6H10O + CH4O

Quantity Value Units Method Reference Comment
Deltar-13.63 ± 0.69kJ/molEqkHine and Arata, 1976liquid phase; ALS

Water + Cyclohexane, 1,1-dimethoxy- = Cyclohexanone + 2Methyl Alcohol

By formula: H2O + C8H16O2 = C6H10O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar28.9 ± 0.1kJ/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

Cyclohexanol + Acetone = Cyclohexanone + Isopropyl Alcohol

By formula: C6H12O + C3H6O = C6H10O + C3H8O

Quantity Value Units Method Reference Comment
Deltar9.9 ± 1.9kJ/molEqkFedoseenko, Yursha, et al., 1983gas phase; At 503 K; ALS

Cyclohexanone + 2Methyl Alcohol = Water + Cyclohexane, 1,1-dimethoxy-

By formula: C6H10O + 2CH4O = H2O + C8H16O2

Quantity Value Units Method Reference Comment
Deltar-54. ± 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

Cyclohexanone + Isopropyl Alcohol = Cyclohexanol + Acetone

By formula: C6H10O + C3H8O = C6H12O + C3H6O

Quantity Value Units Method Reference Comment
Deltar-9.9 ± 1.9kJ/molEqkKabo, Yursha, et al., 1988gas 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]

Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [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]

Kabo G.J., 1988
Kabo G.J., Thermodynamic properties of cyclohexanol and cyclohexanone, J. Chem. Thermodyn., 1988, 20, 429-437. [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]

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

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

Vilcu R., 1975
Vilcu R., Heat capacity of cyclohexanone and 4-methylcyclohexanone in the vapor phase, Rev. Chim. (Bucharest), 1975, 26, 129-131. [all data]

Kabo G.J., 1995
Kabo G.J., Thermodynamic properties, conformation, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-967. [all data]

Rabinovoch, Tel'noy, et al., 1962
Rabinovoch, N.B.; Tel'noy, V.I.; Terman, L.M.; Kirillova, A.S.; Razuvaev, G.A., The heats of decomposition and formation of dicyclohexyl- and dimethylperoxidecarbonate, Dokl. Akad. Nauk SSSR, 1962, 143, 133-136. [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]

Nakamura, Suga, et al., 1980
Nakamura, N.; Suga, H.; Seki, S., Calorimetric study on orientationally disordered crystals. Cyclohexene oxide and cyclohexanone, Bull. Chem. Soc. Japan, 1980, 53(10), 2755-2761. [all data]

Phillip, 1939
Phillip, N.M., Adiabatic and isothermal compressibilities of liquids, Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]

Herz and Bloch, 1924
Herz, W.; Bloch, W., Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe, Z. Phys. Chem., 1924, 110, 23-39. [all data]

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [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]

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]

Hine and Arata, 1976
Hine, J.; Arata, K., Keto-Enol tautomerism. II. The calorimetrical determination of the equilibrium constants for keto-enol tautomerism for cyclohexanone, Bull. Chem. Soc. Jpn., 1976, 49, 3089-3092. [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]

Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions, Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [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]


Notes

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