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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- 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.
Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -30.14 ± 0.38 | kcal/mol | N/A | Spitzer and Huffman, 1947 | Value computed using ΔfHliquid° value of -169.4±1.6 kj/mol from Spitzer and Huffman, 1947 and ΔvapH° value of 43.35±0.21 kj/mol from missing citation.; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 87.66 ± 0.30 | cal/mol*K | N/A | Finke H.L., 1956 | GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.230 | 50. | Dorofeeva O.V., 1986 | S(T) values calculated by [ Stull D.R., 1969] are in good agreement with those selected here; however, the discrepancy in Cp(298.15 K) amounts to 6.2 J/mol*K. S(T) values calculated by molecular mechanics method [ Chang S., 1970] are about 13 J/mol*K less than recommended ones; discrepancies in Cp(T) values amount to 1-2 J/mol*K.; GT |
15.48 | 100. | ||
19.88 | 150. | ||
23.90 | 200. | ||
31.804 | 273.15 | ||
34.9 ± 1.2 | 298.15 | ||
35.179 | 300. | ||
48.317 | 400. | ||
60.485 | 500. | ||
70.899 | 600. | ||
79.680 | 700. | ||
87.108 | 800. | ||
93.427 | 900. | ||
98.822 | 1000. | ||
103.44 | 1100. | ||
107.40 | 1200. | ||
110.81 | 1300. | ||
113.74 | 1400. | ||
116.28 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -40.49 ± 0.39 | kcal/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -40.60 ± 0.60 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1258.5 ± 0.2 | kcal/mol | Ccb | Kaarsemaker and Coops, 1952 | Corresponding ΔfHºliquid = -40.39 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1258.44 ± 0.38 | kcal/mol | Ccb | Spitzer and Huffman, 1947 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1258.35 ± 0.38 kcal/mol; Corresponding ΔfHºliquid = -40.49 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 62.620 | cal/mol*K | N/A | Finke, Scott, et al., 1956 | DH |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1255.4 | kcal/mol | Ccb | Ruzieka and Schlapfer, 1933 | Heat of combustion corrected for pressure; Corresponding ΔfHºsolid = -43.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.573 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
51.513 | 298.15 | Tanaka, 1985 | DH |
51.4964 | 298.15 | Fortier, D'Arcy, et al., 1979 | DH |
51.274 | 298.15 | Wilhelm, Faradjzadeh, et al., 1979 | DH |
51.205 | 298.15 | Jolicoeur, Boileau, et al., 1975 | DH |
51.501 | 298.15 | Finke, Scott, et al., 1956 | T = 12 to 330 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Henry's Law 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: 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
By formula: H2 + C8H14 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.3 | kcal/mol | Chyd | Doering, Roth, et al., 1989 | liquid phase |
ΔrH° | -24.5 ± 0.2 | kcal/mol | Chyd | Roth and Lennartz, 1980 | liquid phase; solvent: Cyclohexane |
ΔrH° | -23.04 ± 0.17 | kcal/mol | Chyd | Rogers, Von Voithenberg, et al., 1978 | liquid phase; solvent: Hexane |
ΔrH° | -23.0 ± 0.1 | kcal/mol | Chyd | Turner and Meador, 1957 | liquid phase; solvent: Acetic acid |
ΔrH° | -23.28 ± 0.15 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -23.53 ± 0.04 kcal/mol; At 355 K |
By formula: H2 + C8H14 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -34.5 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; see Doering, Roth, et al., 1989 |
ΔrH° | -34.41 ± 0.43 | kcal/mol | Chyd | Rogers, Von Voithenberg, et al., 1978 | liquid phase; solvent: Hexane |
ΔrH° | -32.24 ± 0.21 | kcal/mol | Chyd | Turner and Meador, 1957 | liquid phase; solvent: Acetic acid |
By formula: 3H2 + C8H10 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -76.39 ± 0.44 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Acetic acid |
ΔrH° | -72.36 ± 0.26 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
By formula: 2H2 + C8H12 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -69.6 ± 0.2 | kcal/mol | Chyd | Roth, Hopf, et al., 1994 | liquid phase; solvent: Isooctane |
ΔrH° | -69.0 | kcal/mol | Chyd | Turner, Jarrett, et al., 1973 | liquid phase; solvent: Acetic acid |
By formula: C8H12 + 2H2 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -55.0 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
ΔrH° | -53.68 ± 0.02 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid |
By formula: 2H2 + C8H12 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -49.8 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
ΔrH° | -48.96 ± 0.08 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid |
By formula: C8H12 + 2H2 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -52.09 ± 0.28 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid |
By formula: 3H2 + C8H10 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -79.91 ± 0.17 | kcal/mol | Chyd | Turner, Mallon, et al., 1973 | liquid phase; solvent: Glacial acetic acid |
By formula: 4H2 + C8H8 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -97.96 ± 0.05 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
By formula: 4H2 + C8H8 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 152.9 ± 0.3 | kcal/mol | Chyd | Roth, Hopf, et al., 1994 | liquid phase; solvent: Isooctane |
By formula: H2 + C8H14 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.4 ± 0.3 | kcal/mol | Chyd | Rogers and McLafferty, 1971 | liquid phase; solvent: Acetic acid |
By formula: 2H2 + C8H12 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -76.6 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
By formula: 2H2 + C8H12 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -64.7 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
By formula: 2H2 + C8H12 = C8H16
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -67.5 ± 0.1 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
Henry's Law data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
0.0098 | Q | N/A | Several references are given in the list of Henry's law constants but not assigned to specific species. | |
0.0095 | Q | N/A | missing citation give several references for the Henry's law constants but don't assign them to specific species. |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, 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]
Finke H.L., 1956
Finke H.L.,
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]
Dorofeeva O.V., 1986
Dorofeeva O.V.,
Thermodynamic properties of twenty-one monocyclic hydrocarbons,
J. Phys. Chem. Ref. Data, 1986, 15, 437-464. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]
Chang S., 1970
Chang S.,
The heats of combustion and strain energies of bicyclo[n.m.0]alkanes,
J. Am. Chem. Soc., 1970, 92, 3109-3118. [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]
Doering, Roth, et al., 1989
Doering, W.E.; Roth, W.R.; Bauer, F.; Breuckmann, R.; Ebbrecht, T.; Herbold, M.; Schmidt, R.; Lennartz, H-W.; Lenoir, D.; Boese, R.,
Rotational barriers of strained olefines,
Chem. Ber., 1989, 122, 1263-1266. [all data]
Roth and Lennartz, 1980
Roth, W.R.; Lennartz, H.W.,
Heats of hydrogenation. I. Determination of heats of hydrogenation with an isothermal titration calorimeter,
Chem. Ber., 1980, 113, 1806-1817. [all data]
Rogers, Von Voithenberg, et al., 1978
Rogers, D.W.; Von Voithenberg, H.; Allinger, N.L.,
Heats of hydrogenation of the cis and trans isomers of cyclooctene,
J. Org. Chem., 1978, 43, 360-361. [all data]
Turner and Meador, 1957
Turner, R.B.; Meador, W.R.,
Heats of hydrogenation. IV. Hydrogenation of some cis- and trans-cycloolefins,
J. Am. Chem. Soc., 1957, 79, 4133-4136. [all data]
Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A.,
Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes,
J. Am. Chem. Soc., 1939, 61, 1868-1876. [all data]
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Turner, Mallon, et al., 1973
Turner, R.B.; Mallon, B.J.; Tichy, M.; Doering, W.v.E.; Roth, W.R.; Schroder, G.,
Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes,
J. Am. Chem. Soc., 1973, 95, 8605-8610. [all data]
Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W.,
Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds,
J. Am. Chem. Soc., 1957, 79, 4127-4133. [all data]
Roth, Hopf, et al., 1994
Roth, W.R.; Hopf, H.; Horn, C.,
Propargyl-Stabilisierungsenergie,
Chem. Ber., 1994, 127, 1781-1795. [all data]
Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J.,
Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins,
J. Am. Chem. Soc., 1973, 95, 790-792. [all data]
Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J.,
A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring,
Tetrahedron, 1971, 27, 3765-3775. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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 ΔrH° Enthalpy of reaction 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.