Bibenzyl
- Formula: C14H14
- Molecular weight: 182.2610
- IUPAC Standard InChI: InChI=1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
- 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, Condensed phase thermochemistry 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 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, 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 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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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: 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
2 +
=
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, 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, 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, Original value = -25.8 ± 2.0 kcal/mol; At 302 K |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]
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]
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, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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