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
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Other names: Adipic ketone; Adipinketon; Dumasin; Ketocyclopentane; Ketopentamethylene; UN 2245; NSC 4122
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Gas phase thermochemistry data

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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
Δ_fH°_gas	-47.19 ± 0.30	kcal/mol	Cm	Wiberg, Crocker, et al., 1991	ALS
Δ_fH°_gas	-46.55 ± 0.41	kcal/mol	Ccb	Wolf, 1972	ALS
Δ_fH°_gas	-46.12 ± 0.44	kcal/mol	Ccb	Sellers and Sunner, 1962	Reanalyzed by Cox and Pilcher, 1970, Original value = -46.31 kcal/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.156	50.	Thermodynamics Research Center, 1997	p=1 bar. Selected entropies and heat capacities agree within 2 J/molK with statistical values calculated by [ Shvaro O.V., 1987] except for S(1000 K) which value is about 6 J/molK lower than that of [ Thermodynamics Research Center, 1997]. Discrepancies with statistical calculation of [ Andreevskii D.N., 1976] amount to 4-12 J/molK for S(T) and 3-8 J/molK for Cp(T).; GT
10.80	100.
12.89	150.
15.69	200.
20.85	273.15
22.78	298.15
22.93	300.
30.693	400.
37.598	500.
43.363	600.
48.141	700.
52.137	800.
55.507	900.
58.368	1000.
60.805	1100.
62.88	1200.
64.67	1300.
66.23	1400.
67.54	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
27.940	360.	Shvaro O.V., 1987	GT
28.958	375.
30.600	400.
31.993	420.
33.296	440.
34.426	460.
35.664	480.

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-57.40 ± 0.30	kcal/mol	Cm	Wiberg, Crocker, et al., 1991
Δ_fH°_liquid	-56.74 ± 0.40	kcal/mol	Ccb	Wolf, 1972
Δ_fH°_liquid	-56.52	kcal/mol	Ccb	Sellers and Sunner, 1962
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-686.79 ± 0.39	kcal/mol	Ccb	Wolf, 1972	Corresponding Δ_fHº_liquid = -56.728 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-686.91 ± 0.22	kcal/mol	Ccb	Sellers and Sunner, 1962	Corresponding Δ_fHº_liquid = -56.61 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_liquid	-685.9 ± 0.2	kcal/mol	Ccb	Skuratov, Kozina, et al., 1957	At 20C; Corresponding Δ_fHº_liquid = -57.6 kcal/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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Individual Reactions

Cyclopentanone + =

By formula: C₅H₈O + H₂ = C₅H₁₀O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-14.40 ± 0.16	kcal/mol	Cm	Wiberg, Crocker, et al., 1991	liquid phase; ALS
Δ_rH°	-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^- + = Cyclopentanone

By formula: C₅H₇O^- + H⁺ = C₅H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	368.0 ± 4.2	kcal/mol	G+TS	Brickhouse and Squires, 1988	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	360.3 ± 4.0	kcal/mol	IMRB	Brickhouse and Squires, 1988	gas phase; B

= Cyclopentanone +

By formula: C₅H₁₀O = C₅H₈O + H₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	13.1 ± 1.1	kcal/mol	Eqk	Fedoseenko, Yursha, et al., 1984	gas phase; ALS
Δ_rH°	12.26	kcal/mol	Eqk	Cubberley and Mueller, 1946	gas phase; ALS

+ = Cyclopentanone +

By formula: C₆H₁₀O + H₂O = C₅H₈O + CH₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-5.07 ± 0.17	kcal/mol	Cm	Hine and Arata, 1976	liquid phase; Heat of hydrolysis; ALS

+ = Cyclopentanone + 2

By formula: H₂O + C₇H₁₄O₂ = C₅H₈O + 2CH₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	3.9 ± 0.4	kcal/mol	Cm	Wiberg, Morgan, et al., 1994	liquid phase; ALS

Cyclopentanone + 2 = +

By formula: C₅H₈O + 2CH₄O = H₂O + C₇H₁₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.4 ± 0.3	kcal/mol	Cm	Wiberg, Morgan, et al., 1994	gas phase; ALS

+ = + Cyclopentanone

By formula: C₆H₁₀O + C₅H₁₀O = C₆H₁₂O + C₅H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-2.77 ± 0.41	kcal/mol	Eqk	Fedoseenko, Yursha, et al., 1984	gas phase; ALS

References

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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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Shvaro O.V., 1987
Shvaro O.V., Thermodynamic properties of cyclopentanone and cyclohexanone, Inzh.-Fiz. Zh., 1987, 52, 807-812. [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]

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]

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

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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