1,1'-Bicyclohexyl
- Formula: C12H22
- Molecular weight: 166.3031
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 508. ± 10. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 276.9 ± 0.4 | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 276.9 | K | N/A | Pilcher, 1957 | Uncertainty assigned by TRC = 0.002 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 57.98 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 58.0 ± 0.3 | kJ/mol | C | Montgomery, Rossini, et al., 1978 | ALS |
ΔvapH° | 58.0 | kJ/mol | N/A | Montgomery, Rossini, et al., 1978 | DRB |
ΔvapH° | 58.0 ± 0.2 | kJ/mol | C | Montgomery, Rossini, et al., 1978 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
372. to 373. | 0.01 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.8 | 346. | A | Stephenson and Malanowski, 1987 | Based on data from 331. to 511. K.; AC |
50.1 | 435. | N/A | Wieczorek and Kobayashi, 1981 | AC |
42.5 | 525. | N/A | Wieczorek and Kobayashi, 1981 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.86 | 276.8 | AC | Chirico, Cowell, et al., 1998 | Based on data from 6. to 440. K.; AC |
6.78 | 277.2 | DSC | Domalski and Hearing, 1996 | See also O'Rourke and Mraw, 1983.; AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.01 | 256.1 | Domalski and Hearing, 1996 | CAL |
2.77 | 267.5 | ||
25.89 | 273.5 | ||
24.46 | 277.2 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.350 | 256.5 | crystaline, IV | crystaline, III | Horn, Klaeboe, et al., 1992 | DH |
0.320 | 267.0 | crystaline, III | crystaline, II | Horn, Klaeboe, et al., 1992 | DH |
7.090 | 273.6 | crystaline, II | crystaline, I | Horn, Klaeboe, et al., 1992 | DH |
6.610 | 277.4 | crystaline, I | liquid | Horn, Klaeboe, et al., 1992 | Crystal/isotropic liquid transition.; DH |
1.540 | 256.1 | crystaline, IV | crystaline, III | O'Rourke and Mraw, 1983 | DH |
0.740 | 267.5 | crystaline, III | crystaline, II | O'Rourke and Mraw, 1983 | DH |
7.080 | 273.5 | crystaline, II | crystaline, I | O'Rourke and Mraw, 1983 | DH |
6.780 | 277.2 | crystaline, I | liquid | O'Rourke and Mraw, 1983 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
5.3 | 256.5 | crystaline, IV | crystaline, III | Horn, Klaeboe, et al., 1992 | DH |
1.2 | 267.0 | crystaline, III | crystaline, II | Horn, Klaeboe, et al., 1992 | DH |
25.9 | 273.6 | crystaline, II | crystaline, I | Horn, Klaeboe, et al., 1992 | DH |
23.8 | 277.4 | crystaline, I | liquid | Horn, Klaeboe, et al., 1992 | Crystal/isotropic; DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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 |
Gas Chromatography
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 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. | 1313. | Bredael, 1982 | Column length: 100. m; Column diameter: 0.5 mm |
Packed | SE-30 | 150. | 1324. | Shlyakhov, Anvaer, et al., 1975 | |
Capillary | Squalane | 100. | 1309. | Mitra, Mohan, et al., 1974 | H2; Column length: 50. m; Column diameter: 0.2 mm |
Capillary | Squalane | 100. | 1295. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Apiezon L | 100. | 1327. | Besson and Gäumann, 1973 | Column length: 50. m; Column diameter: 0.25 mm |
Packed | SE-30 | 130. | 1284. | Antheaume and Guiochon, 1965 | |
Packed | SE-30 | 170. | 1327. | Antheaume and Guiochon, 1965 | |
Packed | Methyl Silicone | 130. | 1284. | Antheaume and Guiochon, 1965 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1301.5 | 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 | 1301.2 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
Capillary | DB-5 | 1293.1 | 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 | 1301.5 | 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 | 1307.8 | Song, Lai, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | Ultra-1 | 1304.39 | Richmond and Pombo-Villar, 1997 | 25. m/0.32 mm/0.52 μm, 15. K/min, 320. C @ 10. min; Tstart: 35. C |
Capillary | DB-5 | 1293.1 | 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 | 1301.5 | 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 | 1307.8 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 6. K/min; Tstart: 40. C; Tend: 310. C |
Capillary | DB-5 | 1301.5 | 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 | 1301.2 | Lai and Song, 1995 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 310. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1312. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1298. | Woerdenbag, Windono, et al., 2004 | 30. m/0.249 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 300. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1313. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1420. | Peng, Yang, et al., 1991 | Program: not specified |
Capillary | DB-Wax | 1431. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Phase change 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.
Pilcher, 1957
Pilcher, G.,
Anal. Chim. Acta, 1957, 17, 144. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
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]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]
Wieczorek and Kobayashi, 1981
Wieczorek, Stefan A.; Kobayashi, Riki,
Vapor-pressure measurements of 1-methylnaphthalene, 2-methylnaphthalene, and 9,10-dihydrophenanthrene at elevated temperatures,
J. Chem. Eng. Data, 1981, 26, 1, 8-11, https://doi.org/10.1021/je00023a005
. [all data]
Chirico, Cowell, et al., 1998
Chirico, R.D.; Cowell, A.B.; Good, W.D.; Klots, T.D.; Knipmeyer, S.E.; Nguyen, A.; Rau, A.P.; Reynolds, J.W.; Smith, N.K.; Steele, W.V.,
Heat capacities, enthalpy increments, phase transitions, and derived thermodynamic functions for the condensed phases of bicyclohexyl between the temperatures 6 K and 440 K,
The Journal of Chemical Thermodynamics, 1998, 30, 12, 1423-1439, https://doi.org/10.1006/jcht.1998.0399
. [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]
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]
Horn, Klaeboe, et al., 1992
Horn, A.; Klaeboe, P.; Nielsen, C.; Mastryukov, V.S.; Myrvold, B.O.; Redford, K.,
Solid phases of bicyclohexyl studied with vibrational spectroscopy and calorimetry, 1992, Analyst(London) 117(3)355-360. [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]
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]
Mitra, Mohan, et al., 1974
Mitra, G.D.; Mohan, G.; Sinha, A.,
Gas chromatographic analysis of complex hydrocarbon mixtures,
J. Chromatogr. A, 1974, 91, 633-648, https://doi.org/10.1016/S0021-9673(01)97944-0
. [all data]
Besson and Gäumann, 1973
Besson, R.; Gäumann, T.,
Indices de rétention de cycloalcanes, cycloalcènes, bicycloalkyles, cycloalkyl-cycloalcényles et bicycloalcényles en chromatographie en phase gazeuse,
Helv. Chim. Acta, 1973, 56, 3, 1159-1164, https://doi.org/10.1002/hlca.19730560339
. [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]
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]
Richmond and Pombo-Villar, 1997
Richmond, R.; Pombo-Villar, E.,
Short communication. Gas chromatography-mass spectrometry coupled with pseudo-Sadtler retention indices, for the identification of components in the essential oil of Curcuma longa L.,
J. Chromatogr. A, 1997, 760, 2, 303-308, https://doi.org/10.1016/S0021-9673(96)00802-3
. [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, 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]
Woerdenbag, Windono, et al., 2004
Woerdenbag, H.J.; Windono, T.; Bos, R.; Riswan, S.; Quax, W.J.,
Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia,
Flavour Fragr. J., 2004, 19, 2, 145-148, https://doi.org/10.1002/ffj.1284
. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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
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