Benzene, cyclohexyl-
- Formula: C12H16
- Molecular weight: 160.2554
- IUPAC Standard InChI: InChI=1S/C12H16/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1,3-4,7-8,12H,2,5-6,9-10H2
- 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-
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Gas phase 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 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 |
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
3 +
=
By formula: 3H2 + C12H10 = C12H16
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -230. | kJ/mol | Eqk | Frye, 1962 | liquid phase |
3 +
=
By formula: 3H2 + C12H16 = C12H22
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -230. | kJ/mol | Eqk | Frye, 1962 | liquid 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 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 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | SE-30 | 130. | 1314. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
| Packed | SE-30 | 150. | 1326. | Shlyakhov, Anvaer, et al., 1975 | |
| Packed | SE-30 | 200. | 1357. | Shlyakhov, Anvaer, et al., 1975 | |
| Packed | SE-30 | 130. | 1300. | Antheaume and Guiochon, 1965 | |
| Packed | SE-30 | 170. | 1330. | Antheaume and Guiochon, 1965 | |
| Packed | SE-30 | 184. | 1345. | Antheaume and Guiochon, 1965 | |
| Packed | Methyl Silicone | 130. | 1300. | Antheaume and Guiochon, 1965 |
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1296. | Hayes and Pitzer, 1982 | 110. m/0.25 mm/0.20 μm, He, 1. K/min; Tstart: 35. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1308.9 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1317.7 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1322.9 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1308.9 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1317.7 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-5 | 1322.9 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
| Capillary | DB-1 | 1312. | Peng, Hua, et al., 1992 | 30. m/0.32 mm/1.5 μm, 40. C @ 4. min, 8. K/min; Tend: 280. C |
| Capillary | Petrocol DH | 1302. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
| Capillary | OV-101 | 1296. | Hayes and Pitzer, 1981 | 108. m/0.25 mm/0.2 μm, 1. K/min; Tstart: 35. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Packed | SE-30 | 1333. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Supelcowax-10 | 1661. | Chung, Fung, et al., 2005 | 60. m/0.25 mm/0.25 μm, 35. C @ 5. min, 6. K/min, 195. C @ 60. min |
| Capillary | DB-Wax | 1643. | Iwaoka, Hagi, et al., 1994 | He, 40. C @ 5. min, 2. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 200. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH | 1302. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
| Capillary | OV-1 | 1289. | Orav, Kailas, et al., 1999 | 2. K/min; Tstart: 50. C; Tend: 160. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1660. | Peng, Yang, et al., 1991 | Program: not specified |
| Capillary | DB-Wax | 1662. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
Frye, 1962
Frye, C.G.,
Equilibria in the hydrogenation of polycyclic aromatics,
J. Chem. Eng. Data, 1962, 7, 592-595. [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]
Bredael, 1982
Bredael, P.,
Retention indices of hydrocarbons on SE-30,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1982, 5, 6, 325-328, https://doi.org/10.1002/jhrc.1240050610
. [all data]
Shlyakhov, Anvaer, et al., 1975
Shlyakhov, A.F.; Anvaer, B.I.; Zolotareva, O.V.; Romina, N.N.; Novikova, N.V.; Koreshkova, R.I.,
On the possibility of group indentification of hydrocarbons by gas chromatography from temperature coefficients of retention indices,
Zh. Anal. Khim., 1975, 30, 788-792. [all data]
Antheaume and Guiochon, 1965
Antheaume, J.; Guiochon, G.,
Application de la chromatographie en phase gazeuse à l'étude de la composition des fractions moyennes d'un brut pétrolier,
Bull. Soc. Chim. Fr., 1965, 2, 298-307. [all data]
Hayes and Pitzer, 1982
Hayes, P.C., Jr.; Pitzer, E.W.,
Characterizing petroleum- and shale-derived jet fuel distillates via temperature-programmed Kováts indices,
J. Chromatogr., 1982, 253, 179-198, https://doi.org/10.1016/S0021-9673(01)88376-X
. [all data]
Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B.,
Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils
in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]
Lai and Song, 1995
Lai, W.-C.; Song, C.,
Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels,
Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H
. [all data]
Peng, Hua, et al., 1992
Peng, C.T.; Hua, R.L.; Maltby, D.,
Prediction of retention indexes. IV. Chain branching in alkylbenzene isomers with C10-13 alkyl chains identified in a scintillator solvent,
J. Chromatogr., 1992, 589, 1-2, 231-239, https://doi.org/10.1016/0021-9673(92)80027-R
. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Hayes and Pitzer, 1981
Hayes, P.C., Jr.; Pitzer, E.W.,
Kovats indices as a tool in characterizing hydrocarbon fuels in temperature programmed glass capillary gas chromatography. Part 1. Qualitative identification, Inhouse rpt. for Air Force Wright Aeronautical Labs., Air Force Wright Aeronautical Labs., Wright-Patterson AFB, Ohio, 1981, 75. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Chung, Fung, et al., 2005
Chung, H.Y.; Fung, P.K.; Kim, J.-S.,
Aroma impact components in commercial plain sufu,
J. Agric. Food Chem., 2005, 53, 5, 1684-1691, https://doi.org/10.1021/jf048617d
. [all data]
Iwaoka, Hagi, et al., 1994
Iwaoka, W.; Hagi, Y.; Umano, K.; Shibamoto, T.,
Volatile chemicals identified in fresh and cooked breadfruit,
J. Agric. Food Chem., 1994, 42, 4, 975-976, https://doi.org/10.1021/jf00040a026
. [all data]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J.,
Composition of the oil from waste tires. 2. Fraction boiling at 160-180 0C,
Proc. Estonian Acad. Sci. Chem., 1999, 48, 3, 136-140. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy 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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