Cyclohexane, chloro-
- Formula: C6H11Cl
- Molecular weight: 118.605
- IUPAC Standard InChIKey: UNFUYWDGSFDHCW-UHFFFAOYSA-N
- CAS Registry Number: 542-18-7
- 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: Chlorocyclohexane; Cyclohexyl chloride; Monochlorocyclohexane
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Gas phase thermochemistry data
Go To: Top, Phase change 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -166.5 ± 1.9 | kJ/mol | Ccb | An and Guo, 1995 | Author was aware that data differs from previously reported values; HCl(1:600 H2O) |
ΔfH°gas | -163.98 ± 0.62 | kJ/mol | Cm | Diky, Kabo, et al., 1994 | |
ΔfH°gas | -164. ± 3. | kJ/mol | Cm | Kirkbride, 1956 | Heat of formation derived by Cox and Pilcher, 1970 |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
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 | 416. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 230.15 | K | N/A | Timmermans and Hennaut-Roland, 1955 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 230.1 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 228.8 | K | N/A | Crowe and Smyth, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 226. | K | N/A | White and Bishop, 1940 | Crystal phase 1 phase; Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 230.00 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 1.5 K; by cryoscopic; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 229.34 | K | N/A | Diky, Kabo, et al., 1994, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 42. ± 2. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
39.3 | 365. | A | Stephenson and Malanowski, 1987 | Based on data from 350. to 416. K. See also Andreevskii, Brazhnikov, et al., 1969.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
1.67 | 228.7 | DSC | Singh and Murthy, 2008 | AC |
2.04 | 229.3 | AC | Diky, Kabo, et al., 1994 | Based on data from 5. to 304. K.; AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.42 | 120. | Kozyro, Kabo, et al., 1992 | CAL |
36.35 | 220.4 | ||
8.91 | 229.3 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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: C6H11Cl + HCl = C6H12 + Cl2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -143.1 | kJ/mol | Cm | Kirkbride, 1956 | liquid phase |
References
Go To: Top, Gas phase thermochemistry data, Phase change 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.
An and Guo, 1995
An, X.-W.; Guo, D.-J.,
Formation enthalpies and non-bonding interactions of hexachlorocyclohexanes,
Thermochim. Acta, 1995, 253, 235-242. [all data]
Diky, Kabo, et al., 1994
Diky, V.V.; Kabo, G.J.; Kozyro, A.A.; Krasulin, A.P.; Sevruk, V.M.,
Thermodynamic properties of crystalline and liquid chlorocyclohexane and inversion of ring,
J. Chem. Thermodyn., 1994, 26, 1001-1013. [all data]
Kirkbride, 1956
Kirkbride, F.W.,
The heats of chlorination of some hydrocarbons and their chloro-derivatives,
J. Appl. Chem., 1956, 6, 11-21. [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]
Timmermans and Hennaut-Roland, 1955
Timmermans, J.; Hennaut-Roland, M.,
Work of the International Bureau of Physical-Chemical Standards. IX. The Physical Constants of Twenty Organic Compounds,
J. Chim. Phys. Phys.-Chim. Biol., 1955, 52, 223. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Crowe and Smyth, 1951
Crowe, R.W.; Smyth, C.P.,
J. Am. Chem. Soc., 1951, 73, 5406. [all data]
White and Bishop, 1940
White, A.H.; Bishop, W.S.,
Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds,
J. Am. Chem. Soc., 1940, 62, 8-16. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Diky, Kabo, et al., 1994, 2
Diky, V.V.; Kabo, G.J.; Kozyro, A.A.; Krasulin, A.P.; Sevruk, V.M.,
Thermodynamic properties of crystalline and liquid chlorocyclohexane and inversion of ring,
J. Chem. Thermodyn., 1994, 26, 9, 1001, https://doi.org/10.1006/jcht.1994.1117
. [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]
Andreevskii, Brazhnikov, et al., 1969
Andreevskii, D.N.; Brazhnikov, M.M.; Il'inchik, V.N.,
Vestn. Beloruss. Univ., 1969, 2, 1, 3. [all data]
Singh and Murthy, 2008
Singh, L.P.; Murthy, S.S.N.,
Dielectric and Calorimetric Study of Orientationally Disordered Phases in Two Unusual Two-Component Systems,
J. Phys. Chem. B, 2008, 112, 9, 2606-2615, https://doi.org/10.1021/jp077663o
. [all data]
Kozyro, Kabo, et al., 1992
Kozyro, A.A.; Kabo, G.J.; Krouk, V.S.; Sheiman, M.S.; Yursha, I.A.; Simirsky, V.V.; Krasulin, A.P.; Sevruk, V.M.; Gogolinsky, V.I.,
Thermodynamic properties of cyclohexanone oxime,
J. Chem. Thermodyn., 1992, 24, 8, 883, https://doi.org/10.1016/S0021-9614(05)80233-2
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions 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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