1,1'-Bicyclohexyl
- Formula: C12H22
- Molecular weight: 166.3031
- IUPAC Standard InChI: InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
- IUPAC Standard InChIKey: WVIIMZNLDWSIRH-UHFFFAOYSA-N
- CAS Registry Number: 92-51-3
- 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: Bicyclohexyl; Bicyclohexane; Cyclohexane, cyclohexyl-; Dicyclohexane; Dicyclohexyl; Dodecahydrobiphenyl; 1,1'-Biphenyl, dodecahydro-; 1,1-Bicyclohexyl; Cyclohexylcyclohexane; NSC 59855
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Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -66.05 ± 0.74 | kcal/mol | Ccb | Montgomery, Rossini, et al., 1978 | ALS |
| ΔfH°liquid | -65.32 ± 0.29 | kcal/mol | Ccb | Good and Lee, 1976 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1814.03 ± 0.63 | kcal/mol | Ccb | Montgomery, Rossini, et al., 1978 | Corresponding ΔfHºliquid = -66.05 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1814.76 ± 0.24 | kcal/mol | Ccb | Good and Lee, 1976 | Corresponding ΔfHºliquid = -65.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1778.12 | kcal/mol | Ccb | Gollis, Belenyessy, et al., 1962 | Corresponding ΔfHºliquid = -101.96 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1815.6 | kcal/mol | Ccb | Wise, Serijan, et al., 1951 | Corresponding ΔfHºliquid = -64.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1801.5 ± 1.5 | kcal/mol | Ccb | Brull, 1935 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1799.35 kcal/mol; Corresponding ΔfHºliquid = -78.58 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 |
|---|---|---|---|
| 67.64 | 298.15 | O'Rourke and Mraw, 1983 | T = 220 to 475 K. Cp = 0.7589 (T/K) + 56.7 (277.2 to 475 K) J/mol*K.; DH |
| 71.7 | 313. | Gudinowicz, Campbell, et al., 1963 | T = 313 to 483 K.; DH |
| 71.80 | 311. | Gollis, Belenyessy, et al., 1962, 2 | Temperatures 100, 200, 300°F.; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase 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 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
+ 3
=
By formula: C12H16 + 3H2 = C12H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -73.7 ± 0.2 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
+ 3
=
By formula: C12H16 + 3H2 = C12H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -73.4 ± 0.2 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
2 +
=
By formula: 2H2 + C12H18 = C12H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -57.4 ± 0.2 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase |
3 +
=
By formula: 3H2 + C12H16 = C12H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -54. | kcal/mol | Eqk | Frye, 1962 | liquid phase |
Gas phase ion energetics 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 by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 9.41 | PE | Bodor, Dewar, et al., 1970 |
References
Go To: Top, Condensed 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.
Montgomery, Rossini, et al., 1978
Montgomery, R.L.; Rossini, F.D.; Mansson, M.,
Enthalpies of combustion, vaporization, and formation of phenylbenzene, cyclohexylbenzene, and cyclohexylcyclohexane; enthalpy of hydrogenation of certain aromatic systems,
J. Chem. Eng. Data, 1978, 23, 125-129. [all data]
Good and Lee, 1976
Good, W.D.; Lee, S.H.,
The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons,
J. Chem. Thermodyn., 1976, 8, 643-650. [all data]
Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluation of pure hydrocarbons as jet fuels,
J. Chem. Eng. Data, 1962, 7, 331-316. [all data]
Wise, Serijan, et al., 1951
Wise, C.H.; Serijan, K.T.; Goodman, I.A.,
NACA Technical Report 1003,
NACA Technical Report 1003, 1951, 1-10. [all data]
Brull, 1935
Brull, L.,
Sui calori di combustione di alcuni derivati del bifenil,
Gazz. Chim. Ital., 1935, 65, 19-28. [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]
O'Rourke and Mraw, 1983
O'Rourke, D.F.; Mraw, S.C.,
Heat capacities and enthalpies of fusion of dibenzothiophene (220 to 560 K) and of biphenyl, cyclohexylbenzene, and cyclohexylcyclohexane (220 to 475 K). Enthalpies and temperatures of three transitions in solid cyclohexylcyclohexane,
J. Chem. Thermodynam., 1983, 15, 489-502. [all data]
Gudinowicz, Campbell, et al., 1963
Gudinowicz, B.J.; Campbell, R.H.; Adams, J.S.,
Specific heat measurements of complex saturated hydrocarbons,
J. Chem. Eng. Data, 1963, 8, 201-214. [all data]
Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluations of pure hydrocarbons as Jet Fuels,
J. Chem. Eng. Data, 1962, 7, 311-316. [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]
Frye, 1962
Frye, C.G.,
Equilibria in the hydrogenation of polycyclic aromatics,
J. Chem. Eng. Data, 1962, 7, 592-595. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid ΔcH°liquid Enthalpy of combustion of liquid 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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