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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Reaction thermochemistry data
Go To: Top, 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° | 1533. ± 8.4 | kJ/mol | D-EA | Brinkman, Berger, et al., 1993 | gas phase; B |
| ΔrH° | 1531. ± 9.6 | kJ/mol | D-EA | Zimmerman, Jackson, et al., 1978 | gas phase; B |
| ΔrH° | 1544. ± 18. | kJ/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Between acetone, Me2C=NOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1501. ± 9.6 | kJ/mol | H-TS | Brinkman, Berger, et al., 1993 | gas phase; B |
| ΔrG° | 1498. ± 11. | kJ/mol | H-TS | Zimmerman, Jackson, et al., 1978 | gas phase; B |
| ΔrG° | 1511. ± 17. | kJ/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° | -75.86 ± 0.50 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -63.51 ± 0.63 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -64.5 ± 0.3 kJ/mol; At 355 K; ALS |
=
+
By formula: C6H12O = C6H10O + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 63.4 ± 2.3 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; Dehydrogenation; ALS |
+
=
+
By formula: H2O + C7H12O = C6H10O + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -13.63 ± 0.69 | kJ/mol | Eqk | Hine and Arata, 1976 | liquid phase; ALS |
+
=
+ 2
By formula: H2O + C8H16O2 = C6H10O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 28.9 ± 0.1 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
+
=
+
By formula: C6H12O + C3H6O = C6H10O + C3H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 9.9 ± 1.9 | kJ/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° | -54. ± 1. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
+
=
+
By formula: C6H10O + C5H10O = C6H12O + C5H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -11.6 ± 1.7 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
+
=
+
By formula: C6H10O + C3H8O = C6H12O + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.9 ± 1.9 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
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]
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, Reaction thermochemistry data, References
- Symbols used in this document:
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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