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:
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.
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Options:
- Switch to SI units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes

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.

Phase change data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes

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
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity	Value	Units	Method	Reference	Comment
T_boil	469.2	K	N/A	Weast and Grasselli, 1989	BS
T_boil	478.7	K	N/A	Wolf, 1972, 2	Uncertainty assigned by TRC = 0.5 K; TRC
T_boil	469.15	K	N/A	Wallach, 1907	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	317.4	K	N/A	Wolf, 1972, 2	Uncertainty assigned by TRC = 0.1 K; TRC
T_fus	298.65	K	N/A	Wallach, 1907	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	13.0	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. to 383. K.; AC
Δ_vapH°	12.8	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. to 383. K.; AC
Δ_vapH°	13.0	kcal/mol	CGC	Chickos, Hosseini, et al., 1995	Based on data from 343. to 383. K.; AC
Δ_vapH°	11.6 ± 0.1	kcal/mol	N/A	Wolf, 1972	AC
Δ_vapH°	13.0 ± 0.5	kcal/mol	V	Ruzieka and Schlapfer, 1933	Heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
11.3	338.	A	Stephenson and Malanowski, 1987	Based on data from 323. to 403. K.; AC
11.2	409.	A,EB	Stephenson and Malanowski, 1987	Based on data from 394. to 484. K. See also Meyer and Hotz, 1976.; AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
3.44	174.	Gonthier-Vassal and Szwarc, 1998	CAL
14.5	226.8
2.2	318.7

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

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

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

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

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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Wolf, 1972, 2
Wolf, G., Thermochemical studies of cyclic ketones, Helv. Chim. Acta, 1972, 55, 1446. [all data]

Wallach, 1907
Wallach, O., Justus Liebigs Ann. Chem., 1907, 353, 331. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [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]

Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, A.; Szwarc, H., Thermochim. Acta, 1998, 141. [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

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

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fusS	Entropy of fusion
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
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.