Benzene, cyclohexyl-
- Formula: C12H16
- Molecular weight: 160.2554
- IUPAC Standard InChIKey: IGARGHRYKHJQSM-UHFFFAOYSA-N
- CAS Registry Number: 827-52-1
- 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: Cyclohexane, phenyl-; Cyclohexylbenzene; Phenylcyclohexane; 1,1'-Biphenyl, 1,2,3,4,5,6-hexahydro-
- 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, Phase change 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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -16.7 ± 1.5 | kJ/mol | Ccb | Montgomery, Rossini, et al., 1978 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -19.2 ± 5.6 kJ/mol; ALS |
ΔfH°gas | -14.2 | kJ/mol | N/A | Good and Lee, 1976 | Value computed using ΔfHliquid° value of -76.6±1.1 kj/mol from Good and Lee, 1976 and ΔvapH° value of 62.4 kj/mol from Montgomery, Rossini, et al., 1978.; DRB |
Phase change data
Go To: Top, Gas 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 512.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 508.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 513.27 | K | N/A | Mears, Stanley, et al., 1963 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tboil | 513.27 | K | N/A | Jessup and Stanley, 1961 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 280.3 ± 0.6 | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 61. ± 2. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
400.7 | 0.040 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
56.4 | 348. | N/A | Sohda, Okazaki, et al., 1990 | Based on data from 333. to 343. K.; AC |
51.3 | 436. | A | Stephenson and Malanowski, 1987 | Based on data from 421. to 513. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
340.7 to 513. | 4.98206 | 2339.819 | -42.881 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.270 | 280.5 | O'Rourke and Mraw, 1983 | DH |
15.3 | 280.5 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.44 | 280.5 | O'Rourke and Mraw, 1983 | DH |
Gas phase ion energetics 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference |
---|---|---|
8.1 | EI | Mikaya, Zaikin, et al., 1979 |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C8H8+ | 9.99 ± 0.02 | C4H8 | EI | Zaikin, Mikaya, et al., 1981 | |
C8H8+ | 10.8 | C4H8 | EI | Mikaya, Zaikin, et al., 1979 | |
C9H9+ | 11.7 | C3H7 | EI | Mikaya, Zaikin, et al., 1979 |
References
Go To: Top, Gas phase thermochemistry data, Phase change 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]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Mears, Stanley, et al., 1963
Mears, T.W.; Stanley, C.L.; Compere, E.L.; Howard, F.L.,
Synthesis, purification, and physical properties of seven twelve-carbon hyd rocarbons,
J. Res. Natl. Bur. Stand., Sect. A, 1963, 67, 475. [all data]
Jessup and Stanley, 1961
Jessup, R.S.; Stanley, C.L.,
Heats and volumes of mixing in several c(12) hydrocarbon systems,
J. Chem. Eng. Data, 1961, 6, 368-71. [all data]
Sohda, Okazaki, et al., 1990
Sohda, M.; Okazaki, M.; Iwai, Y.; Arai, Y.; Sakoguchi, A.; Ueoka, R.; Kato, Y.,
Vapor pressures of cyclohexylbenzene and diphenylmethane,
The Journal of Chemical Thermodynamics, 1990, 22, 6, 607-608, https://doi.org/10.1016/0021-9614(90)90152-G
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [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]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Mikaya, Zaikin, et al., 1979
Mikaya, A.I.; Zaikin, V.G.; Finkel'stein, E.S.; Vdovin, V.M.,
Mass-spectrometric investigation of aromatic derivatives of cycloalkanes and cycloalkanols,
Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 10, 2221. [all data]
Zaikin, Mikaya, et al., 1981
Zaikin, V.G.; Mikaya, A.I.; Finkel'shtein, E.Sh.; Vdovin, V.M.; Nametkin, N.S.,
Heats of formation of phenylcycloalkanes,
Dokl. Phys. Chem., 1981, 253, 620. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization 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.