Cyclopentanone
- Formula: C5H8O
- Molecular weight: 84.1164
- IUPAC Standard InChI: InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
- IUPAC Standard InChIKey: BGTOWKSIORTVQH-UHFFFAOYSA-N
- CAS Registry Number: 120-92-3
- 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: Adipic ketone; Adipinketon; Dumasin; Ketocyclopentane; Ketopentamethylene; UN 2245; NSC 4122
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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
+
=
By formula: C5H8O + H2 = C5H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -14.40 ± 0.16 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -12.25 ± 0.15 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -12.50 ± 0.06 kcal/mol; At 355 K; ALS |
C5H7O- + =
By formula: C5H7O- + H+ = C5H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 368.0 ± 4.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 360.3 ± 4.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; B |
=
+
By formula: C5H10O = C5H8O + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 13.1 ± 1.1 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
| ΔrH° | 12.26 | kcal/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
+
=
+
By formula: C6H10O + H2O = C5H8O + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.07 ± 0.17 | kcal/mol | Cm | Hine and Arata, 1976 | liquid phase; Heat of hydrolysis; ALS |
+
=
+ 2
By formula: H2O + C7H14O2 = C5H8O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 3.9 ± 0.4 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
+ 2
=
+
By formula: C5H8O + 2CH4O = H2O + C7H14O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10.4 ± 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 |
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.
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]
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]
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]
Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B.,
Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol,
J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]
Hine and Arata, 1976
Hine, J.; Arata, K.,
Keto-Enol tautomerism. I. The calorimetrical determination of the equilibrium constant for keto-enol tautomerism for cyclopentanone and acetone,
Bull. Chem. Soc. Jpn., 1976, 49, 3085-3088. [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]
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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