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:
Data at NIST subscription sites:
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.
Phase change data
Go To: Top, References, Notes
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:
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 |
|---|---|---|---|---|---|
| Tboil | 469.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 478.7 | K | N/A | Wolf, 1972 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tboil | 469.15 | K | N/A | Wallach, 1907 | Uncertainty assigned by TRC = 3. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 317.4 | K | N/A | Wolf, 1972 | Uncertainty assigned by TRC = 0.1 K; TRC |
| Tfus | 298.65 | K | N/A | Wallach, 1907 | Uncertainty assigned by TRC = 2. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 13.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
| ΔvapH° | 12.8 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
| ΔvapH° | 13.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 343. to 383. K.; AC |
| ΔvapH° | 11.6 ± 0.1 | kcal/mol | N/A | Wolf, 1972, 2 | AC |
| ΔvapH° | 13.0 ± 0.5 | kcal/mol | V | Ruzieka and Schlapfer, 1933 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
| ΔvapH (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
| ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 3.44 | 174. | Gonthier-Vassal and Szwarc, 1998 | CAL |
| 14.5 | 226.8 | ||
| 2.2 | 318.7 |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
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]
Wolf, 1972, 2
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]
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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° 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.