Cyclooctane
- Formula: C8H16
- Molecular weight: 112.2126
- IUPAC Standard InChIKey: WJTCGQSWYFHTAC-UHFFFAOYSA-N
- CAS Registry Number: 292-64-8
- 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. - Other names: Octamethylene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -169.4 ± 1.6 | kJ/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -169.9 ± 2.5 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5265.7 ± 0.9 | kJ/mol | Ccb | Kaarsemaker and Coops, 1952 | Corresponding ΔfHºliquid = -169.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -5265.3 ± 1.6 | kJ/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5264.9 ± 1.6 kJ/mol; Corresponding ΔfHºliquid = -169.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 262.00 | J/mol*K | N/A | Finke, Scott, et al., 1956 | DH |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -5252.6 | kJ/mol | Ccb | Ruzieka and Schlapfer, 1933 | Heat of combustion corrected for pressure; Corresponding ΔfHºsolid = -182. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
215.78 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
215.53 | 298.15 | Tanaka, 1985 | DH |
215.461 | 298.15 | Fortier, D'Arcy, et al., 1979 | DH |
214.53 | 298.15 | Wilhelm, Faradjzadeh, et al., 1979 | DH |
214.24 | 298.15 | Jolicoeur, Boileau, et al., 1975 | DH |
215.48 | 298.15 | Finke, Scott, et al., 1956 | T = 12 to 330 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 422. ± 6. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 285. ± 5. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 287.94 | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; TRC |
Ttriple | 287.98 | K | N/A | Finke, Scott, et al., 1956, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 287.940 | K | N/A | Waddington, 1955 | Uncertainty assigned by TRC = 0.05 K; date of correspondence not given on card; TRC |
Ttriple | 287.970 | K | N/A | Waddington, 1955 | Uncertainty assigned by TRC = 0.02 K; date of correspondence not given on card; TRC |
Ttriple | 288.0 | K | N/A | Kaarsemaker, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 647.2 ± 0.5 | K | N/A | Daubert, 1996 | |
Tc | 674.2 | K | N/A | Young, 1972 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tc | 647.2 | K | N/A | Hicks and Young, 1971 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 35.6 ± 0.4 | bar | N/A | Daubert, 1996 | |
Pc | 35.50 | bar | N/A | Young, 1972 | Uncertainty assigned by TRC = 0.40 bar; TRC |
Pc | 35.60 | bar | N/A | Hicks and Young, 1971 | Uncertainty assigned by TRC = 0.4053 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.410 | l/mol | N/A | Daubert, 1996 | |
Vc | 0.411 | l/mol | N/A | Young, 1972 | Uncertainty assigned by TRC = 0.007 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.44 ± 0.04 | mol/l | N/A | Daubert, 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 43.35 ± 0.21 | kJ/mol | V | Finke, Scott, et al., 1956, 3 | ALS |
ΔvapH° | 43.3 ± 0.2 | kJ/mol | N/A | Finke, Scott, et al., 1956 | AC |
ΔvapH° | 44.7 | kJ/mol | V | Kaarsemaker and Coops, 1952 | ALS |
ΔvapH° | 43.5 | kJ/mol | E | Spitzer and Huffman, 1947 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
424.2 | 0.987 | Aldrich Chemical Company Inc., 1990 | BS |
421.7 | 0.999 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
40.3 | 373. | N/A | Wu, Locke, et al., 1991 | Based on data from 358. to 413. K.; AC |
43.3 | 304. | A | Stephenson and Malanowski, 1987 | Based on data from 289. to 369. K.; AC |
39.4 | 384. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 369. to 467. K. See also Finke, Scott, et al., 1956.; AC |
39.3 | 388. | EB | Meyer and Hotz, 1976 | Based on data from 373. to 434. K.; AC |
43.1 | 306. | N/A | Anand, Grolier, et al., 1975 | Based on data from 291. to 323. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
369.86 to 467.6 | 3.98805 | 1438.687 | -63.024 | Finke, Scott, et al., 1956 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
58.7 | 166. | B | Bondi, 1963 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.41 | 288. | Acree, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
6.3057 | 166.5 | crystaline, III | crystaline, II | Finke, Scott, et al., 1956 | DH |
0.4782 | 183.8 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
2.4096 | 287.98 | crystaline, I | liquid | Finke, Scott, et al., 1956 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
37.87 | 166.5 | crystaline, III | crystaline, II | Finke, Scott, et al., 1956 | DH |
2.60 | 183.8 | crystaline, II | crystaline, I | Finke, Scott, et al., 1956 | DH |
8.37 | 287.98 | crystaline, I | liquid | Finke, Scott, et al., 1956 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References, Notes
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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.75 ± 0.04 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.82 ± 0.05 | EI | Holmes and Lossing, 1991 | LL |
9.75 | EQ | Sieck and Mautner(Meot-Ner), 1982 | LBLHLM |
9.74 ± 0.05 | PI | Golubitskii, Kulikov, et al., 1979 | LLK |
10.08 ± 0.05 | EI | Puttemans, 1974 | LLK |
9.80 | PE | Puttemans, 1974 | LLK |
9.7 | PE | Batich, Bischof, et al., 1973 | LLK |
Mass spectrum (electron ionization)
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 826 |
NIST MS number | 228916 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spitzer and Huffman, 1947
Spitzer, R.; Huffman, H.M.,
The heats of combustion of cyclopentane, cyclohexane, cycloheptane and cyclooctane,
J. Am. Chem. Soc., 1947, 69, 211-213. [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]
Kaarsemaker and Coops, 1952
Kaarsemaker, S.; Coops, J.,
Thermal quantities of some cycloparaffins. Part III. Results of measurements,
Rec. Trav. Chim. Pays/Bas, 1952, 71, 261. [all data]
Finke, Scott, et al., 1956
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-5476. [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]
Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I.,
Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K,
J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]
Tanaka, 1985
Tanaka, R.,
Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K,
J. Chem. Eng. Data, 1985, 30, 267-269. [all data]
Fortier, D'Arcy, et al., 1979
Fortier, J.-L.; D'Arcy, P.J.; Benson, G.C.,
Heat capacities of binary cycloalkane mixtures at 298.15 K,
Thermochim. Acta, 1979, 28, 37-43. [all data]
Wilhelm, Faradjzadeh, et al., 1979
Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E.,
Molar excess heat capacities and excess volumes of 1,2-dichloroethane + cyclooctane, + mesitylene, and + tetrachloromethane,
J. Chem. Thermodynam., 1979, 11, 979-984. [all data]
Jolicoeur, Boileau, et al., 1975
Jolicoeur, C.; Boileau, J.; Bazinet, S.; Picker, P.,
Thermodynamic properties of aqueous organic solutes in relation to their structure. Part II. Apparent molal volumes and heat capacities of c-alkylamine hydrobromides in water,
Can. J. Chem., 1975, 53, 716-722. [all data]
Finke, Scott, et al., 1956, 2
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, Cyclooctane and 1,3,5-Cycloheptatriene. Low Temperature Thermal Properties, Vapor Pressure and Derived Chemical Thermodynamic Prop.,
J. Am. Chem. Soc., 1956, 78, 5469. [all data]
Waddington, 1955
Waddington, G.,
Personal Commun., 1955. [all data]
Kaarsemaker, 1951
Kaarsemaker, S.,
, Thesis, 1951. [all data]
Daubert, 1996
Daubert, T.E.,
Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes,
J. Chem. Eng. Data, 1996, 41, 365-372. [all data]
Young, 1972
Young, C.L.,
Gas-liquid critical properties of the cycloalkanes and their mixtures,
Aust. J. Chem., 1972, 25, 1625-30. [all data]
Hicks and Young, 1971
Hicks, C.P.; Young, C.L.,
Critical Temperatures of Mixtures of Quasi-spherical Molecules. Alicyclic Hydrocarbons + Benzene, + Hexafluorobenzene and + Perfluorocyclohexane,
Trans. Faraday Soc., 1971, 67, 1605-11. [all data]
Finke, Scott, et al., 1956, 3
Finke, H.L.; Scott, D.W.; Gross, M.E.; Messerly, J.F.; Waddington, G.,
Cycloheptane, cyclooctane and 1,3,5-cycloheptatriene. Low temperature thermal properties, vapor pressure and derived chemical thermodynamic properties,
J. Am. Chem. Soc., 1956, 78, 5469-54. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Wu, Locke, et al., 1991
Wu, Huey S.; Locke, William E.; Sandler, Stanley I.,
Isothermal vapor-liquid equilibrium of binary mixtures containing morpholine,
J. Chem. Eng. Data, 1991, 36, 1, 127-130, https://doi.org/10.1021/je00001a037
. [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]
Anand, Grolier, et al., 1975
Anand, Subhash C.; Grolier, Jean P.E.; Kiyohara, Osamu; Halpin, Carl J.; Benson, George C.,
Thermodynamic properties of some cycloalkane-cycloalkanol systems at 298. 15K. III,
J. Chem. Eng. Data, 1975, 20, 2, 184-189, https://doi.org/10.1021/je60065a020
. [all data]
Bondi, 1963
Bondi, A.,
Heat of Siblimation of Molecular Crystals: A Catalog of Molecular Structure Increments.,
J. Chem. Eng. Data, 1963, 8, 3, 371-381, https://doi.org/10.1021/je60018a027
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P.,
Ionization energies of homologous organic compounds and correlation with molecular size,
Org. Mass Spectrom., 1991, 26, 537. [all data]
Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M.,
Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions,
J. Phys. Chem., 1982, 86, 3646. [all data]
Golubitskii, Kulikov, et al., 1979
Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N.,
Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]
Puttemans, 1974
Puttemans, J.P.,
Ionisation de cycloalcanes (C5 a C12) en spectroscopie photoelectronique et par impact electronique,
Ing. Chim. (Brussels), 1974, 56, 64. [all data]
Batich, Bischof, et al., 1973
Batich, C.; Bischof, P.; Heilbronner, E.,
The photoelectron spectra of cyclooctatetraene and its hydrogenated derivatives,
J. Electron Spectrosc. Relat. Phenom., 1973, 1, 333. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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