Bibenzyl
- Formula: C14H14
- Molecular weight: 182.2610
- IUPAC Standard InChIKey: QWUWMCYKGHVNAV-UHFFFAOYSA-N
- CAS Registry Number: 103-29-7
- 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: Benzene, 1,1'-(1,2-ethanediyl)bis-; s-Diphenylethane; Dibenzil; Dibenzyl; Ethane, 1,2-diphenyl-; 1,2-Diphenylethane; Benzene, (phenylethyl)-; 1,2-Diphenylethane(sym); 1,2-Diphenylethane, s; sym-Diphenylethane; Dihydrostilbene; NSC 30686
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Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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 | 32.41 ± 0.31 | kcal/mol | Ccb | Coleman and Pilcher, 1966 | ALS |
ΔfH°gas | 30.83 | kcal/mol | N/A | Parks, West, et al., 1946 | Value computed using ΔfHsolid° value of 44.9±3.1 kj/mol from Parks, West, et al., 1946 and ΔsubH° value of 84.1 kj/mol from Coleman and Pilcher, 1966.; DRB |
Phase change data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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
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 | 556. ± 5. | K | AVG | N/A | Average of 23 out of 24 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 325. ± 1. | K | AVG | N/A | Average of 189 out of 195 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 324.340 | K | N/A | Messerly, Finke, et al., 1988 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 21.9 ± 0.2 | kcal/mol | B | Osborn and Scott, 1980 | AC |
ΔsubH° | 21.84 ± 0.11 | kcal/mol | V | Morawetz, 1972 | ALS |
ΔsubH° | 21.8 ± 0.1 | kcal/mol | C | Morawetz, 1972, 2 | AC |
ΔsubH° | 20.1 | kcal/mol | N/A | Coleman and Pilcher, 1966 | DRB |
ΔsubH° | 17.5 ± 0.2 | kcal/mol | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.1 | 398. | GC | Lei, Chankalal, et al., 2002 | Based on data from 323. to 473. K.; AC |
15.3 | 373. | N/A | Sasse, N'guimbi, et al., 1989 | Based on data from 333. to 413. K.; AC |
16.14 ± 0.024 | 324.4 | V | Messerly, Finke, et al., 1988 | ALS |
15.8 ± 0.05 | 340. | N/A | Messerly, Finke, et al., 1988, 2 | AC |
14. | 374. | A | Stephenson and Malanowski, 1987 | Based on data from 359. to 557. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
360.0 to 557. | 4.85526 | 2572.151 | -27.406 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.2 | 308. | EM | Sasse, N'guimbi, et al., 1989 | Based on data from 293. to 323. K.; AC |
21.8 ± 0.1 | 295. | N/A | Kratt, Beckhaus, et al., 1983 | Based on data from 273. to 318. K.; AC |
20.07 ± 0.11 | 326.2 | V | Aihara, 1959 | crystal phase; ALS |
20.1 ± 0.1 | 286. to 307. | V | Aihara, 1959, 2 | See also Cox and Pilcher, 1970.; AC |
17.3 ± 0.31 | 304. | ME | Bloink, Pausacker, et al., 1951 | Based on data from 290. to 317. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.433 | 324.3 | Domalski and Hearing, 1996 | AC |
5.4995 | 324.4 | Schmidt, 1941 | DH |
5.3951 | 324.3 | Ferry and Thomas, 1933 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
16.9 | 324.4 | Schmidt, 1941 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.97 | 273.2 | Domalski and Hearing, 1996 | CAL |
16.75 | 324.3 |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.537178 | 273.150 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1988, 2 | DH |
5.432725 | 324.348 | crystaline, I | liquid | Messerly, Finke, et al., 1988, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.97 | 273.150 | crystaline, II | crystaline, I | Messerly, Finke, et al., 1988, 2 | DH |
16.75 | 324.348 | crystaline, I | liquid | Messerly, Finke, et al., 1988, 2 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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: 2H2 + C14H10 = C14H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -59.64 ± 0.56 | kcal/mol | Chyd | Davis, Allinger, et al., 1985 | liquid phase; solvent: Hexane |
ΔrH° | -64.2 ± 1.1 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | solid phase; Reanalyzed by Cox and Pilcher, 1970, 2, Original value = -64.1 ± 1.1 kcal/mol |
By formula: C14H12 + H2 = C14H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -18.59 ± 0.20 | kcal/mol | Chyd | Williams, 1942 | liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, 2, Original value = -20.14 ± 0.36 kcal/mol; At 302 K |
By formula: H2 + C14H12 = C14H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -31.44 ± 0.20 | kcal/mol | Chyd | Williams, 1942 | liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, 2, Original value = -25.8 ± 2.0 kcal/mol; At 302 K |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 113286 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Coleman and Pilcher, 1966
Coleman, D.J.; Pilcher, G.,
Heats of combustion of biphenyl, bibenzyl, naphthalene, anthracene, and phenanthrene,
Trans. Faraday Soc., 1966, 62, 821-827. [all data]
Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A.,
Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols,
J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]
Messerly, Finke, et al., 1988
Messerly, J.F.; Finke, H.L.; Good, W.D.; Gammon, B.E.,
Condensed-phase heat capacities and derived thermodynamic properties for 1,4-dimethylbenzene, 1,2-diphenylethane, and 2,3-dimethylnaphthalene,
J. Chem. Thermodyn., 1988, 20, 485. [all data]
Osborn and Scott, 1980
Osborn, A.G.; Scott, D.W.,
Vapor pressures of 17 miscellanenous organic compounds,
J. Chem. Thermodyn., 1980, 12, 429-438. [all data]
Morawetz, 1972
Morawetz, E.,
Enthalpies of vaporization for a number of aromatic compounds,
J. Chem. Thermodyn., 1972, 4, 455. [all data]
Morawetz, 1972, 2
Morawetz, Ernst,
Enthalpies of vaporization for a number of aromatic compounds,
The Journal of Chemical Thermodynamics, 1972, 4, 3, 455-460, https://doi.org/10.1016/0021-9614(72)90029-8
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank,
Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons,
J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148
. [all data]
Sasse, N'guimbi, et al., 1989
Sasse, K.; N'guimbi, J.; Jose, J.; Merlin, J.C.,
Tension de vapeur d'hydrocarbures polyaromatiques dans le domaine 10-3--10 Torr,
Thermochimica Acta, 1989, 146, 53-61, https://doi.org/10.1016/0040-6031(89)87075-3
. [all data]
Messerly, Finke, et al., 1988, 2
Messerly, J.F.; Finke, H.L.; Good, W.D.; Gammon, B.E.,
Condensed-phase heat capacities and derived thermodynamic properties for 1,4-dimethylbenzene, 1,2-diphenylethane, and 2,3-dimethylnaphthalene,
J. Chem. Thermodynam., 1988, 20, 485-501. [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]
Kratt, Beckhaus, et al., 1983
Kratt, G.; Beckhaus, H.D.; Bernioehr, W.; Ruechardt, C.,
Thermolabile hydrocarbons. XVII. Enthalpies of combustion and formation of ten sym-tetraalkyl-1,2-diarylethanes,
Thermochim. Acta, 1983, 62, 279-294. [all data]
Aihara, 1959
Aihara, A.,
Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy,
Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]
Aihara, 1959, 2
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy,
Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Bloink, Pausacker, et al., 1951
Bloink, G.J.; Pausacker, K.H.; Jones, A.S.; Lee, W.A.; Peacocke, A.R.; Bright, Norman F.H.; Moffatt, J.S.; Wilkinson, J.H.,
Notes,
J. Chem. Soc., 1951, 622, https://doi.org/10.1039/jr9510000622
. [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]
Schmidt, 1941
Schmidt, W.R.,
Thesis Washington University (St. Louis), 1941. [all data]
Ferry and Thomas, 1933
Ferry, J.D.; Thomas, S.B.,
Some heat capacity data for durene, pentamethylbenzene, stilbene, and dibenzyl,
J. Phys. Chem., 1933, 37, 253-255. [all data]
Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W.,
Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone,
J. Org. Chem., 1985, 50, 3601-3604. [all data]
Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A.,
Heats of hydrogenation Part 2.-Acetylene derivatives,
Trans. Faraday Soc., 1958, 54, 47-53. [all data]
Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Williams, 1942
Williams, R.B.,
Heats of catalytic hydrogenation in solution. I. Apparatus, technique, and the heats of hydrogenation of certain pairs of stereoisomers,
J. Am. Chem. Soc., 1942, 64, 1395-1404. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), 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 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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