Cyclooctanone

Formula: C₈H₁₄O
Molecular weight: 126.1962
IUPAC Standard InChI: InChI=1S/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-7H2
IUPAC Standard InChIKey: IIRFCWANHMSDCG-UHFFFAOYSA-N
CAS Registry Number: 502-49-8
Chemical structure:
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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	-65.05 ± 0.42	kcal/mol	Ccb	Wolf, 1972	Hfusion=0.655±0.025 kcal/mol; ALS
Δ_fH°_gas	-64.9 ± 1.3	kcal/mol	Ccb	Ruzieka and Schlapfer, 1933	Heat of formation derived by Cox and Pilcher, 1970; ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
10.1	50.	Thermodynamics Research Center, 1997	p=1 bar.; GT
14.7	100.
19.7	150.
24.98	200.
33.72	273.15
36.90	298.15
37.14	300.
49.98	400.
61.52	500.
71.27	600.
79.42	700.
86.26	800.
92.07	900.
96.96	1000.
101.2	1100.
104.8	1200.
107.8	1300.
110.5	1400.
112.8	1500.

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	-77.9 ± 1.2	kcal/mol	Ccb	Ruzieka and Schlapfer, 1933	Heat of formation derived by Cox and Pilcher, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-77.03 ± 0.39	kcal/mol	Ccb	Wolf, 1972	Hfusion=0.655±0.025 kcal/mol
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1153.34 ± 0.38	kcal/mol	Ccb	Wolf, 1972	Hfusion=0.655±0.025 kcal/mol; Corresponding Δ_fHº_solid = -77.275 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_solid	-1152.7 ± 1.2	kcal/mol	Ccb	Ruzieka and Schlapfer, 1933	Reanalyzed by Cox and Pilcher, 1970, Original value = -1152. kcal/mol; Corresponding Δ_fHº_solid = -77.91 kcal/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

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Data compiled by: 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

+ Cyclooctanone =

By formula: H₂ + C₈H₁₄O = C₈H₁₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-13.32	kcal/mol	Chyd	Wiberg, Crocker, et al., 1991	liquid phase
Δ_rH°	-12.70	kcal/mol	Chyd	Wiberg, Crocker, et al., 1991	solid phase
Δ_rH°	-9.31	kcal/mol	Chyd	Wiberg, Crocker, et al., 1991	gas phase
Δ_rH°	-12.70 ± 0.14	kcal/mol	Cm	Wiberg, Crocker, et al., 1991	solid phase

References

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Wolf, 1972
Wolf, G., Thermochemische Untersuchungen an cyclischen Ketonen, Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]

Ruzieka and Schlapfer, 1933
Ruzieka, L.; Schlapfer, P., Zur kenntnis des kohlenstoffringes XXII. Uber die verbrennungswarme bei hochgliedrigen ringverbindungen, Helv. Chim. Acta, 1933, 16, 162-169. [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]

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]

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
Δ_cH°_solid	Enthalpy of combustion of solid 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_fH°_solid	Enthalpy of formation of solid 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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