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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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)

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	403. ± 1.	K	AVG	N/A	Average of 13 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	221.7	K	N/A	Wurflinger and Kreutzenbeck, 1978	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	220.05	K	N/A	Sellers and Sunner, 1962	Uncertainty assigned by TRC = 0.5 K; TRC
T_fus	222.6	K	N/A	Anonymous, 1954	Uncertainty assigned by TRC = 0.6 K; TRC
T_fus	221.85	K	N/A	Timmermans, 1952	Uncertainty assigned by TRC = 0.4 K; TRC
T_fus	221.85	K	N/A	Timmermans and Hennaut-Roland, 1937	Uncertainty assigned by TRC = 0.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	221.44	K	N/A	Shvaro, 1987	Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	624.5	K	N/A	Ambrose and Ghiassee, 1987	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	45.40	atm	N/A	Ambrose and Ghiassee, 1987	Uncertainty assigned by TRC = 0.49 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	10.2 ± 0.1	kcal/mol	AVG	N/A	Average of 6 values; Individual data points

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
9.92	338.	EB	Teodorescu, Barhala, et al., 2006	Based on data from 323. to 403. K.; AC
9.70	332.	N/A	Ambrose and Ghiassee, 1987, 2	Based on data from 317. to 427. K.; AC
10.2	308.	A	Stephenson and Malanowski, 1987	Based on data from 293. to 404. K.; AC
9.46	353.	A,EB	Stephenson and Malanowski, 1987	Based on data from 338. to 416. K. See also Meyer and Hotz, 1976.; AC
8.688	403.7	N/A	Majer and Svoboda, 1985
10.4	286.	N/A	Benson and Kistiakowsky, 1942	Based on data from 273. to 299. K.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
273.09 to 298.79	1.07734	376.418	-168.499	Benson and Kistiakowsky, 1942	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.72	221.2	Gonthier-Vassal and Szwarc, 1998	AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

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

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

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes

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]

Wurflinger and Kreutzenbeck, 1978
Wurflinger, Alber (see wuerfl a); Kreutzenbeck, J., J. Phys. Chem. Solids, 1978, 39, 193. [all data]

Anonymous, 1954
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 13, Ohio State Univ., 1954. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Timmermans and Hennaut-Roland, 1937
Timmermans, J.; Hennaut-Roland, M., Works from International Bureau at Physical-Chemical Standards. VIII. Physical constants of 20 organic compounds, J. Chim. Phys. Phys.-Chim. Biol., 1937, 34, 693. [all data]

Shvaro, 1987
Shvaro, O.V., Thermodynamics of some cyclic and acyclic ketones and alcohols C4-C7, Ph.D. Thesis, Byeloruss. State Univ., Minsk, 1987. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of C5 and C6 Cyclic Alcohols and Ketones, J. Chem. Thermodyn., 1987, 19, 903. [all data]

Teodorescu, Barhala, et al., 2006
Teodorescu, Mariana; Barhala, Alexandru; Dragoescu, Dana, Isothermal (vapour+liquid) equilibria for the binary (cyclopentanone or cyclohexanone with 1,1,2,2-tetrachloroethane) systems at temperatures of (343.15, 353.15, and 363.15)K, The Journal of Chemical Thermodynamics, 2006, 38, 11, 1432-1437, https://doi.org/10.1016/j.jct.2006.01.010 . [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of C5 and C6 cyclic alcohols and ketones, The Journal of Chemical Thermodynamics, 1987, 19, 9, 903-909, https://doi.org/10.1016/0021-9614(87)90036-X . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A., Cohesive energies in polar organic liquids. 3. Cyclic ketones, J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035 . [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Benson and Kistiakowsky, 1942
Benson, S.W.; Kistiakowsky, G.B., The Photochemical Decomposition of Cyclic Ketones, J. Am. Chem. Soc., 1942, 64, 1, 80-86, https://doi.org/10.1021/ja01253a021 . [all data]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, Anne; Szwarc, Henri, Thermodynamic properties of cycloketones: A DSC study, Thermochimica Acta, 1998, 320, 1-2, 141-154, https://doi.org/10.1016/S0040-6031(98)00409-2 . [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
P_c	Critical pressure
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
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_fusH	Enthalpy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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