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
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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:
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 |
|---|---|---|---|---|---|
| ΔfH°gas | -65.05 ± 0.42 | kcal/mol | Ccb | Wolf, 1972 | Hfusion=0.655±0.025 kcal/mol; ALS |
| ΔfH°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
| Cp,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 compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°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 |
| ΔfH°solid | -77.03 ± 0.39 | kcal/mol | Ccb | Wolf, 1972 | Hfusion=0.655±0.025 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1153.34 ± 0.38 | kcal/mol | Ccb | Wolf, 1972 | Hfusion=0.655±0.025 kcal/mol; Corresponding ΔfHºsolid = -77.275 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -1152.7 ± 1.2 | kcal/mol | Ccb | Ruzieka and Schlapfer, 1933 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1152. kcal/mol; Corresponding ΔfHºsolid = -77.91 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
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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, 2 | 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, 2 | 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 | 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 |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H14O+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 203.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 195.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.28 | PE | Spanka, Boese, et al., 1987 | Vertical value; LBLHLM |
| 9.28 | PE | Spanka and Rademacher, 1986 | Vertical value; LBLHLM |
| 9.08 | PE | Kovac and Klasinc, 1978 | Vertical value; LLK |
| 9.00 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
| 9.09 ± 0.02 | PE | Chadwick, Frost, et al., 1971 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Spanka, Boese, et al., 1987
Spanka, G.; Boese, R.; Rademacher, P.,
Transannualr interactions in difunctional medium rings. 2. Molecular structure and conformational properties of 1-alkylhexahydroazocin-5-ones,
J. Org. Chem., 1987, 52, 3362. [all data]
Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P.,
Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy,
J. Org. Chem., 1986, 51, 592. [all data]
Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L.,
Photoelectron spectroscopy of adamantane and some adamantanones,
Croat. Chem. Acta, 1978, 51, 55. [all data]
Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen,
J. Mol. Struct., 1974, 21, 231. [all data]
Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L.,
The photoelectron spectra of cyclic ketones,
Tetrahedron Lett., 1971, 47, 4543. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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
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