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, 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 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 | -69. ± 2. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 84.567 | cal/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 (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 31.716 | 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 |
| 31.914 | 300. | ||
| 42.208 | 400. | ||
| 51.726 | 500. | ||
| 59.794 | 600. | ||
| 66.532 | 700. | ||
| 72.115 | 800. | ||
| 76.666 | 900. | ||
| 80.621 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas 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 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 | -84.13 ± 0.16 | kcal/mol | Cac | Wiberg, Wasserman, et al., 1985 | Trifluoroacetolysis; ALS |
| ΔfH°liquid | -83.6 ± 0.5 | kcal/mol | Ccb | Rabinovoch, Tel'noy, et al., 1962 | ALS |
| ΔfH°liquid | -83.03 ± 0.53 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -83.23 kcal/mol; ALS |
| ΔfH°liquid | -83.45 ± 0.04 | kcal/mol | Ccb | Parks, Mosley, et al., 1950 | ALS |
| ΔfH°liquid | -85.84 | kcal/mol | Ccb | Kelley, 1929 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -891. ± 5. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 48.726 | cal/mol*K | N/A | Adachi, Suga, et al., 1968 | DH |
| S°liquid | 47.71 | cal/mol*K | N/A | Kelley, 1929 | Average of values derived from measurements on both low and high temperature crystal forms down to 13 K, plus entropy of transition and fusion. Debye extrapolation below 13.5 K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 51.162 | 298.15 | Mayer, Rachwalska, et al., 1990 | T = 170 to 320 K. Cp(liq) = -2223.2606 + 22.0059595T - 0.0691686793T2 + 0.0000763592T3 J/mol*K (298 to 320 K). Cp value caluculated from equation.; DH |
| 50.189 | 298.15 | Caceres-Alonso, Costas, et al., 1988 | DH |
| 52.61 | 298. | Conti, Gianni, et al., 1976 | DH |
| 50.7 | 297.95 | Petit and TerMinassian, 1974 | T = 297 to 428 K. Value is unsmoothed experimental datum.; DH |
| 51.049 | 300. | Adachi, Suga, et al., 1968 | T = 14 to 320 K.; DH |
| 48.40 | 305.1 | Phillip, 1939 | DH |
| 49.959 | 298.15 | Kelley, 1929 | T = 13 to 300 K. Value is unsmoothed experimental datum.; DH |
| 41.80 | 290. | Herz and Bloch, 1924 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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: 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° | -18.13 ± 0.12 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase |
| ΔrH° | -15.18 ± 0.15 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -15.42 ± 0.08 kcal/mol; At 355 K |
+
=
+
By formula: C6H12O + C4F6O3 = C8H11F3O2 + C2HF3O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -21.524 ± 0.037 | kcal/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; Trifluoroacetolysis |
=
+
By formula: C6H12O = C6H10O + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.2 ± 0.55 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; Dehydrogenation |
+
=
+
By formula: C6H12O + C3H6O = C6H10O + C3H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 2.4 ± 0.45 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 503 K |
=
+
By formula: C6H12O = C6H12 + H2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15.2 ± 0.55 | kcal/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° | -2.77 ± 0.41 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase |
+
=
+
By formula: C6H10O + C3H8O = C6H12O + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.4 ± 0.45 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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, 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]
Rabinovoch, Tel'noy, et al., 1962
Rabinovoch, N.B.; Tel'noy, V.I.; Terman, L.M.; Kirillova, A.S.; Razuvaev, G.A.,
The heats of decomposition and formation of dicyclohexyl- and dimethylperoxidecarbonate,
Dokl. Akad. Nauk SSSR, 1962, 143, 133-136. [all data]
Sellers and Sunner, 1962
Sellers, P.; Sunner, S.,
Heats of combustion of cyclic ketones and alcohols,
Acta Chem. Scand., 1962, 16, 46-52. [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]
Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr.,
Heats of combustion and formation of some organic compounds containing oxygen,
J. Chem. Phys., 1950, 18, 152. [all data]
Kelley, 1929
Kelley, K.K.,
Cyclohexanol and the third law of thermodynamics,
J. Am. Chem. Soc., 1929, 51, 1400-1406. [all data]
Adachi, Suga, et al., 1968
Adachi, K.; Suga, H.; Seki, S.,
Phase changes in crystalline and glassy-crystalline cyclohexanol,
Bull. Chem. Soc. Japan, 1968, 41, 1073-1087. [all data]
Mayer, Rachwalska, et al., 1990
Mayer, J.; Rachwalska, M.; Sciesinska, E.; Sciesinski, J.,
On the polymorphism of solid cyclohexanol by adiabatic calorimetry and far infrared methods,
J. Phys.(Paris), 1990, 51(9), 857-867. [all data]
Caceres-Alonso, Costas, et al., 1988
Caceres-Alonso, M.; Costas, M.; Andreoli-Ball, L.; Patterson, D.,
Steric effects on the self-association of branched and cyclic alcohols in inert solvents. Apparent heat capacities of secondary and tertiary alcohols in hydrocarbons,
Can. J. Chem., 1988, 66, 989-998. [all data]
Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M.,
Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C,
Chim. Ind. (Milan), 1976, 58, 225. [all data]
Petit and TerMinassian, 1974
Petit, J.C.; TerMinassian, L.,
Measurements of (dV/dT)p, (dV/dP)T, and (dH/dT)p by flux calorimetry,
J. Chem. Thermodynam., 1974, 6, 1139-1152. [all data]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]
Herz and Bloch, 1924
Herz, W.; Bloch, W.,
Physikalisch-chemische Untersuchungen an Verbindungen der Cyklohexanreihe,
Z. Phys. Chem., 1924, 110, 23-39. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 ΔcH°liquid Enthalpy of combustion of liquid 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
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