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
The 3d structure may be viewed using Java or Javascript. - 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, Reaction 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 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 | -55.23 ± 0.21 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°gas | -53.94 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | ALS |
| ΔfH°gas | -54.43 ± 0.45 | kcal/mol | Ccb | Wolf, 1972 | ALS |
| ΔfH°gas | -54.09 | kcal/mol | Ccb | Sellers and Sunner, 1962 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 80.194 | cal/mol*K | N/A | Kabo G.J., 1988 | GT |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 28.934 | 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 |
| 29.132 | 300. | ||
| 38.690 | 400. | ||
| 46.938 | 500. | ||
| 53.834 | 600. | ||
| 59.577 | 700. | ||
| 64.405 | 800. | ||
| 68.478 | 900. | ||
| 71.955 | 1000. |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 37.094 | 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 |
| 38.497 | 400. | ||
| 40.387 | 420. | ||
| 42.020 | 440. | ||
| 43.893 | 460. | ||
| 45.454 | 480. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction 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 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 | -66.00 ± 0.20 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°liquid | -65.16 ± 0.42 | kcal/mol | Ccb | Wolf, 1972 | ALS |
| ΔfH°liquid | -60.7 ± 0.5 | kcal/mol | Ccb | Rabinovoch, Tel'noy, et al., 1962 | ALS |
| ΔfH°liquid | -64.86 | kcal/mol | Ccb | Sellers and Sunner, 1962 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -840.74 ± 0.41 | kcal/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -65.147 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -845.2 ± 0.5 | kcal/mol | Ccb | Rabinovoch, Tel'noy, et al., 1962 | Corresponding ΔfHºliquid = -60.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -841.04 ± 0.25 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Corresponding ΔfHºliquid = -64.84 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -836.4 ± 0.2 | kcal/mol | Ccb | Skuratov, Kozina, et al., 1957 | At 20C; Corresponding ΔfHºliquid = -69.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 54.739 | cal/mol*K | N/A | Nakamura, Suga, et al., 1980 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 42.352 | 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 |
| 47.90 | 304.2 | Phillip, 1939 | DH |
| 42.50 | 290. | Herz and Bloch, 1924 | DH |
Reaction thermochemistry 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 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- + =
By formula: C6H9O- + H+ = C6H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 366.4 ± 2.0 | kcal/mol | D-EA | Brinkman, Berger, et al., 1993 | gas phase; B |
| ΔrH° | 365.8 ± 2.3 | kcal/mol | D-EA | Zimmerman, Jackson, et al., 1978 | gas phase; B |
| ΔrH° | 369.0 ± 4.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Between acetone, Me2C=NOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 358.7 ± 2.3 | kcal/mol | H-TS | Brinkman, Berger, et al., 1993 | gas phase; B |
| ΔrG° | 358.0 ± 2.6 | kcal/mol | H-TS | Zimmerman, Jackson, et al., 1978 | gas phase; B |
| ΔrG° | 361.2 ± 4.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; Between acetone, Me2C=NOH; B |
+
=
By formula: C6H10O + H2 = C6H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -18.13 ± 0.12 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -15.18 ± 0.15 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -15.42 ± 0.08 kcal/mol; At 355 K; ALS |
=
+
By formula: C6H12O = C6H10O + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.2 ± 0.55 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; Dehydrogenation; ALS |
+
=
+
By formula: H2O + C7H12O = C6H10O + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.26 ± 0.17 | kcal/mol | Eqk | Hine and Arata, 1976 | liquid phase; ALS |
+
=
+ 2
By formula: H2O + C8H16O2 = C6H10O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 6.90 ± 0.03 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
+
=
+
By formula: C6H12O + C3H6O = C6H10O + C3H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 2.4 ± 0.45 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 503 K; ALS |
+ 2
=
+
By formula: C6H10O + 2CH4O = H2O + C8H16O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.9 ± 0.3 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
+
=
+
By formula: C6H10O + C5H10O = C6H12O + C5H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.77 ± 0.41 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
+
=
+
By formula: C6H10O + C3H8O = C6H12O + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.4 ± 0.45 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | gas 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
- 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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