Cyclohexanol
- Formula: C6H12O
- Molecular weight: 100.1589
- IUPAC Standard InChI: InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
- IUPAC Standard InChIKey: HPXRVTGHNJAIIH-UHFFFAOYSA-N
- CAS Registry Number: 108-93-0
- 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: Cyclohexyl alcohol; Adronal; Adronol; Anol; Hexahydrophenol; Hexalin; Hydroxycyclohexane; Naxol; Phenol, hexahydro-; 1-Cyclohexanol; Cyclohexane, hydroxy-; Hydralin; Cicloesanolo; Cykloheksanol; Hydrophenol; NSC 403656
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -290. ± 8. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 353.83 | J/mol*K | N/A | Kabo G.J., 1988 | Other entropy value at 298.15 K obtained from calorimetric data is 327.69 J/mol*K [ Stull D.R., 1969].; GT |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 132.70 | 298.15 | Kabo G.J., 1988 | Statistically calculated S(T) and Cp(T) values given in [ Thermodynamics Research Center, 1997] are 1-10 and 5-10 J/mol*K, respectively, lower than those of [ Kabo G.J., 1988].; GT |
| 133.53 | 300. | ||
| 176.60 | 400. | ||
| 216.42 | 500. | ||
| 250.18 | 600. | ||
| 278.37 | 700. | ||
| 301.73 | 800. | ||
| 320.77 | 900. | ||
| 337.32 | 1000. |
Reaction 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
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: C6H10O + H2 = C6H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -75.86 ± 0.50 | kJ/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase |
| ΔrH° | -63.51 ± 0.63 | kJ/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -64.5 ± 0.3 kJ/mol; At 355 K |
+
=
+
By formula: C6H12O + C4F6O3 = C8H11F3O2 + C2HF3O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -90.06 ± 0.15 | kJ/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; Trifluoroacetolysis |
=
+
By formula: C6H12O = C6H10O + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 63.4 ± 2.3 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; Dehydrogenation |
+
=
+
By formula: C6H12O + C3H6O = C6H10O + C3H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 9.9 ± 1.9 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 503 K |
=
+
By formula: C6H12O = C6H12 + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 63.4 ± 2.3 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 502 K |
+
=
+
By formula: C6H10O + C5H10O = C6H12O + C5H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -11.6 ± 1.7 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase |
+
=
+
By formula: C6H10O + C3H8O = C6H12O + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.9 ± 1.9 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase |
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 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.75 | EI | Rabbih and Selim, 1983 | LBLHLM |
| 10.0 ± 0.2 | EI | Derrick, Holmes, et al., 1975 | LLK |
| 10.0 | EI | Ward and Williams, 1969 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H5O+ | 11.5 | ? | EI | Ward and Williams, 1969 | RDSH |
| C5H7+ | 10.9 | CH3+H2O | EI | Ward and Williams, 1969 | RDSH |
| C6H10+ | 10.4 ± 0.05 | H2O | EI | Green, Bafus, et al., 1975 | LLK |
| C6H10+ | 10.2 ± 0.2 | H2O | EI | Derrick, Holmes, et al., 1975 | LLK |
| C6H10+ | 9.47 | H2O | EI | Lewis and Hamill, 1970 | RDSH |
| C6H10+ | 10.4 ± 0.05 | H2O | EI | Green, 1980 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
Kabo G.J., 1988
Kabo G.J.,
Thermodynamic properties of cyclohexanol and cyclohexanone,
J. Chem. Thermodyn., 1988, 20, 429-437. [all data]
Stull D.R., 1969
Stull D.R., Jr.,
The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [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]
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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A.,
Enthalpies of hydration of alkenes. 3. Cycloalkenes,
J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]
Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I.,
Thermodynamic properties of cyclohexanol and cyclohexanone,
J. Chem. Thermodyn., 1988, 20, 429-437. [all data]
Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions,
Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]
Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system,
Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [all data]
Rabbih and Selim, 1983
Rabbih, M.A.; Selim, E.T.M.,
A Mass spectrometric appearance energies study of cyclohexanol,
Egypt. J. Phys., 1983, 14, 243. [all data]
Derrick, Holmes, et al., 1975
Derrick, P.J.; Holmes, J.L.; Morgan, R.P.,
Kinetics and mechanisms of the loss of water from the cyclohexanol radical ion at times from 50 picoseconds to 10 microseconds following field ionization,
J. Am. Chem. Soc., 1975, 97, 4936. [all data]
Ward and Williams, 1969
Ward, R.S.; Williams, D.H.,
A study of water elimination as a function of ion lifetime in the mass spectrum of cyclohexanol,
J. Organometal. Chem., 1969, 34, 3373. [all data]
Green, Bafus, et al., 1975
Green, M.M.; Bafus, D.; Franklin, J.L.,
Short communication; Combined deuterium labeling and appearance potential measurements to uncover competing reaction mechanisms in the electron- impact-induced loss of water from cyclohexanol,
Org. Mass Spectrom., 1975, 10, 679. [all data]
Lewis and Hamill, 1970
Lewis, D.; Hamill, W.H.,
Excited states of neutral molecular fragments from appearance potentials by electron impact in a mass spectrometer,
J. Chem. Phys., 1970, 52, 6348. [all data]
Green, 1980
Green, M.M.,
A stereochemical bridge between mass spectrometry and free radical chemistry,
Tetrahedron, 1980, 36, 2687. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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