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
Δfgas-231.1 ± 0.88kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfgas-225.7kJ/molEqkKabo, Yursha, et al., 1988ALS
Δfgas-227.7 ± 1.9kJ/molCcbWolf, 1972ALS
Δfgas-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

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes

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
Δfliquid-276.1 ± 0.84kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfliquid-272.6 ± 1.8kJ/molCcbWolf, 1972ALS
Δfliquid-254. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962ALS
Δfliquid-271.4kJ/molCcbSellers and Sunner, 1962ALS
Quantity Value Units Method Reference Comment
Δcliquid-3517.6 ± 1.7kJ/molCcbWolf, 1972Corresponding Δfliquid = -272.58 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3536. ± 2.kJ/molCcbRabinovoch, Tel'noy, et al., 1962Corresponding Δfliquid = -254. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3518.9 ± 1.0kJ/molCcbSellers and Sunner, 1962Corresponding Δfliquid = -271.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-3499. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding Δfliquid = -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

Gas phase ion energetics data

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

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.16 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)841.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity811.2kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.0033EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 3.3 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.18PELoudet, Grimaud, et al., 1976LLK
9.5 ± 0.2EIFortin, Forest, et al., 1973LLK
9.16 ± 0.01PECocksey, Eland, et al., 1971LLK
9.14 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.14 ± 0.03PIVilesov, 1960RDSH
9.29PESpanka and Rademacher, 1986Vertical value; LBLHLM
9.18PEKovac and Klasinc, 1978Vertical value; LLK
9.28PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.14 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

De-protonation reactions

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Δr1533. ± 8.4kJ/molD-EABrinkman, Berger, et al., 1993gas phase; B
Δr1531. ± 9.6kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Δr1544. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Δr1501. ± 9.6kJ/molH-TSBrinkman, Berger, et al., 1993gas phase; B
Δr1498. ± 11.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase; B
Δr1511. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics 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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Loudet, Grimaud, et al., 1976
Loudet, M.; Grimaud, M.; Metras, F.; Pfister-Guillouzo, G., Interactions intramoleculaires en serie cyclohexanique partie II. Spectres photoelectroniques de chloro-2-cyclohexanones, J. Mol. Struct., 1976, 35, 213. [all data]

Fortin, Forest, et al., 1973
Fortin, C.J.; Forest, M.; Vaziri, C.; Gravel, D.; Rousseau, Y., Spectrometrie de masse des cyclohexanones gem-diphenylees. I. Localisation de la charge positive, Can. J. Chem., 1973, 51, 3445. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P., Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy, J. Org. Chem., 1986, 51, 592. [all data]

Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L., Photoelectron spectroscopy of adamantane and some adamantanones, Croat. Chem. Acta, 1978, 51, 55. [all data]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L., The photoelectron spectra of cyclic ketones, Tetrahedron Lett., 1971, 47, 4543. [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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References