Cyclopentanone
- Formula: C5H8O
- Molecular weight: 84.1164
- 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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Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -240.2 ± 1.3 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | |
ΔfH°liquid | -237.4 ± 1.7 | kJ/mol | Ccb | Wolf, 1972 | |
ΔfH°liquid | -236.5 | kJ/mol | Ccb | Sellers and Sunner, 1962 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2873.5 ± 1.6 | kJ/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -237.35 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -2874.0 ± 0.92 | kJ/mol | Ccb | Sellers and Sunner, 1962 | Corresponding ΔfHºliquid = -236.9 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -2870. ± 0.8 | kJ/mol | Ccb | Skuratov, Kozina, et al., 1957 | At 20C; Corresponding ΔfHºliquid = -241. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Reaction 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
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° | -60.25 ± 0.67 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
ΔrH° | -51.25 ± 0.63 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -52.3 ± 0.3 kJ/mol; At 355 K; ALS |
C5H7O- + =
By formula: C5H7O- + H+ = C5H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1540. ± 18. | kJ/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1507. ± 17. | kJ/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; B |
By formula: C5H10O = C5H8O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.9 ± 4.7 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
ΔrH° | 51.30 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
By formula: C6H10O + H2O = C5H8O + CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -21.22 ± 0.69 | kJ/mol | Cm | Hine and Arata, 1976 | liquid phase; Heat of hydrolysis; ALS |
By formula: H2O + C7H14O2 = C5H8O + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 16. ± 2. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
By formula: C5H8O + 2CH4O = H2O + C7H14O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -44. ± 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 |
Mass spectrum (electron ionization)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
NIST MS number | 61744 |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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]
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]
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]
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, Condensed phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid 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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