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
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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 | 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 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1807.5 ± 1.8 | kcal/mol | Ccb | Banse and Parks, 1933 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1806.97 kcal/mol; Corresponding ΔfHºliquid = 12.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 12.31 ± 0.31 | kcal/mol | Ccb | Coleman and Pilcher, 1966 | ALS |
ΔfH°solid | 10.72 ± 0.73 | kcal/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = 10.53 ± 0.004 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1807.24 ± 0.26 | kcal/mol | Ccb | Coleman and Pilcher, 1966 | Corresponding ΔfHºsolid = 12.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1806.8 ± 0.24 | kcal/mol | Ccb | Coops, Mulder, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1807. ± 0.2 kcal/mol; See Coops, Mulder, et al., 1946; Corresponding ΔfHºsolid = 11.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1740. | kcal/mol | Ccb | Serijan and Wise, 1951 | Corresponding ΔfHºsolid = -55. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1815.1 | kcal/mol | Ccb | Wise, Serijan, et al., 1951 | Corresponding ΔfHºsolid = 20.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1805.64 ± 0.72 | kcal/mol | Ccb | Parks, West, et al., 1946 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1805.48 ± 0.72 kcal/mol; Corresponding ΔfHºsolid = 10.72 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 63.9080 | cal/mol*K | N/A | Messerly, Finke, et al., 1988 | crystaline, I phase; DH |
S°solid,1 bar | 64.60 | cal/mol*K | N/A | Huffman, Parks, et al., 1930 | Extrapolation below 90 K, 90.37 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
60.6511 | 298.15 | Messerly, Finke, et al., 1988 | crystaline, I phase; T = 10 to 400 K.; DH |
76.51 | 330. | Kurbatov, 1950 | Temperature 54 to 254°C. Mp = 52.8°C.; DH |
60.21 | 298.1 | Schmidt, 1941 | T = 20 to 200°C, equations only in t°C. Cp(c) = 0.2867 + 0.001743t cal/g*K (20 to 51°C); Cp(liq) = 0.3865 + 0.0005986t cal/g*K (51 to -200°C).; DH |
61.42 | 303. | Ferry and Thomas, 1933 | T = 303 to 343 K.; DH |
60.61 | 298.5 | Smith and Andrews, 1931 | T = 102 to 299 K. Value is unsmoothed experimental datum.; DH |
59.99 | 293.6 | Huffman, Parks, et al., 1930 | T = 93 to 294 K. Value is unsmoothed experimental datum.; DH |
Phase change 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:
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, 2 | 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, 2 | ALS |
15.8 ± 0.05 | 340. | N/A | Messerly, Finke, et al., 1988 | 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, 2.; 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 | DH |
5.432725 | 324.348 | crystaline, I | liquid | Messerly, Finke, et al., 1988 | 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 | DH |
16.75 | 324.348 | crystaline, I | liquid | Messerly, Finke, et al., 1988 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 191.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 185.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.00 ± 0.05 | EI | Pignataro, Mancini, et al., 1972 | LLK |
8.7 ± 0.1 | EI | McLafferty, Wachs, et al., 1970 | RDSH |
9.1 | PE | Pignataro, Mancini, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 10.6 | C7H7 | EI | McLafferty, Wachs, et al., 1970 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed 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.
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]
Banse and Parks, 1933
Banse, H.; Parks, G.S.,
Thermal data on organic compounds. XII. The heats of combustion of nine hydrocarbons,
J. Am. Chem. Soc., 1933, 55, 3223-3227. [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]
Coops, Mulder, et al., 1953
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
Thermochemical investigations on arylethanes I. Heats of combustion of phenylethanes.,
Rec. Trav. Chim. Pays/Bas, 1953, 72, 785. [all data]
Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J.,
The heats of combustion of a number of hydrocarbons,
Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]
Serijan and Wise, 1951
Serijan, K.T.; Wise, P.H.,
Dicyclic hydrocarbons. III. Diphenyl- and dicyclohexylalkanes through C15,
J. Am. Chem. Soc., 1951, 73, 4766-4769. [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]
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. Thermodynam., 1988, 20, 485-501. [all data]
Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C.,
Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons,
J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]
Kurbatov, 1950
Kurbatov, V.Ya.,
Specific heats of liquids. III. Specific heat of hydrocarbons with several noncondensed rings,
Zhur. Obshch. Khim., 1950, 20, 1139-1144. [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]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. I. Phenyl derivatives of methane,
ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [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. 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]
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, 2
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Pignataro, Mancini, et al., 1972
Pignataro, S.; Mancini, V.; Innorta, G.; Distefano, G.,
Ionization energies and ring orbital interaction in diarylmethanes and diaryleth,
Z. Naturforsch., 1972, 27, 534. [all data]
McLafferty, Wachs, et al., 1970
McLafferty, F.W.; Wachs, T.; Lifshitz, C.; Innorta, G.; Irving, P.,
Substituent effects in unimolecular ion decompositions. XV. Mechanistic interpretations and the quasi-equilibrium theory,
J. Am. Chem. Soc., 1970, 92, 6867. [all data]
Pignataro, Mancini, et al., 1971
Pignataro, S.; Mancini, V.; Ridyard, J.N.A.; Lempka, H.J.,
Photoelectron energy spectra of molecules having classically non-conjugated π-systems,
Chem. Commun., 1971, 142. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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