Cyclohexanone
- Formula: C6H10O
- Molecular weight: 98.1430
- IUPAC Standard InChI: InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
- IUPAC Standard InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N
- CAS Registry Number: 108-94-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
View 3d structure (requires JavaScript / HTML 5) - Other names: Anon; Anone; Hexanon; Hytrol O; Nadone; Pimelic ketone; Pimelin ketone; Sextone; Ketohexamethylene; Cicloesanone; Cyclohexanon; Cykloheksanon; NCI-C55005; Rcra waste number U057; UN 1915; Cyclohexyl ketone; NSC 5711
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -231.1 ± 0.88 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°gas | -225.7 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | ALS |
| ΔfH°gas | -227.7 ± 1.9 | kJ/mol | Ccb | Wolf, 1972 | ALS |
| ΔfH°gas | -226.3 | kJ/mol | Ccb | Sellers and Sunner, 1962 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 335.53 | J/mol*K | N/A | Kabo G.J., 1988 | GT |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 121.06 | 298.15 | Kabo G.J., 1988 | Selected 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 |
| 121.89 | 300. | ||
| 161.88 | 400. | ||
| 196.39 | 500. | ||
| 225.24 | 600. | ||
| 249.27 | 700. | ||
| 269.47 | 800. | ||
| 286.51 | 900. | ||
| 301.06 | 1000. |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 155.20 | 385. | Shvaro O.V., 1987 | The 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 |
| 161.07 | 400. | ||
| 168.98 | 420. | ||
| 175.81 | 440. | ||
| 183.65 | 460. | ||
| 190.18 | 480. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -276.1 ± 0.84 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°liquid | -272.6 ± 1.8 | kJ/mol | Ccb | Wolf, 1972 | ALS |
| ΔfH°liquid | -254. ± 2. | kJ/mol | Ccb | Rabinovoch, Tel'noy, et al., 1962 | ALS |
| ΔfH°liquid | -271.4 | kJ/mol | Ccb | Sellers and Sunner, 1962 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3517.6 ± 1.7 | kJ/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -272.58 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3536. ± 2. | kJ/mol | Ccb | Rabinovoch, Tel'noy, et al., 1962 | Corresponding ΔfHºliquid = -254. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3518.9 ± 1.0 | kJ/mol | Ccb | Sellers and Sunner, 1962 | Corresponding ΔfHºliquid = -271.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3499. ± 0.8 | kJ/mol | Ccb | Skuratov, Kozina, et al., 1957 | At 20C; Corresponding ΔfHºliquid = -291. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 229.03 | J/mol*K | N/A | Nakamura, Suga, et al., 1980 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 177.20 | 300. | Nakamura, Suga, et al., 1980 | T = 13 to 300 K. Unsmoothed experimental datum for Cp at 296.40 K is 175.96 J/mol*K.; DH |
| 200.4 | 304.2 | Phillip, 1939 | DH |
| 177.8 | 290. | Herz and Bloch, 1924 | DH |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, 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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, IR Spectrum, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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