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Bibenzyl

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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
Deltafgas135.6 ± 1.3kJ/molCcbColeman and Pilcher, 1966ALS
Deltafgas129.0kJ/molN/AParks, West, et al., 1946Value computed using «DELTA»fHsolid° value of 44.9±3.1 kj/mol from Parks, West, et al., 1946 and «DELTA»subH° value of 84.1 kj/mol from Coleman and Pilcher, 1966.; DRB

Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltacliquid-7562.6 ± 7.5kJ/molCcbBanse and Parks, 1933Reanalyzed by Cox and Pilcher, 1970, Original value = -7560.36 kJ/mol; Corresponding «DELTA»fliquid = 52.63 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid51.5 ± 1.3kJ/molCcbColeman and Pilcher, 1966ALS
Deltafsolid44.9 ± 3.1kJ/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = 44.06 ± 0.02 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-7561.5 ± 1.1kJ/molCcbColeman and Pilcher, 1966Corresponding «DELTA»fsolid = 51.55 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-7559.6 ± 1.0kJ/molCcbCoops, Mulder, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -7559. ± 1. kJ/mol; See Coops, Mulder, et al., 1946; Corresponding «DELTA»fsolid = 49.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-7280.kJ/molCcbSerijan and Wise, 1951Corresponding «DELTA»fsolid = -230. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-7594.4kJ/molCcbWise, Serijan, et al., 1951Corresponding «DELTA»fsolid = 84.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-7554.8 ± 3.0kJ/molCcbParks, West, et al., 1946Reanalyzed by Cox and Pilcher, 1970, Original value = -7554.1 ± 3.0 kJ/mol; Corresponding «DELTA»fsolid = 44.85 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar267.391J/mol*KN/AMesserly, Finke, et al., 1988crystaline, I phase; DH
solid,1 bar270.3J/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 90.37 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
253.764298.15Messerly, Finke, et al., 1988crystaline, I phase; T = 10 to 400 K.; DH
320.1330.Kurbatov, 1950Temperature 54 to 254°C. Mp = 52.8°C.; DH
251.9298.1Schmidt, 1941T = 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
257.0303.Ferry and Thomas, 1933T = 303 to 343 K.; DH
253.6298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH
251.0293.6Huffman, Parks, et al., 1930T = 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

2Hydrogen + Diphenylacetylene = Bibenzyl

By formula: 2H2 + C14H10 = C14H14

Quantity Value Units Method Reference Comment
Deltar-249.5 ± 2.3kJ/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane
Deltar-268.6 ± 4.6kJ/molChydFlitcroft and Skinner, 1958solid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -268. ± 4.6 kJ/mol

(E)-Stilbene + Hydrogen = Bibenzyl

By formula: C14H12 + H2 = C14H14

Quantity Value Units Method Reference Comment
Deltar-77.78 ± 0.84kJ/molChydWilliams, 1942liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -84.2 ± 1.5 kJ/mol; At 302 K

Hydrogen + cis-Stilbene = Bibenzyl

By formula: H2 + C14H12 = C14H14

Quantity Value Units Method Reference Comment
Deltar-131.5 ± 0.84kJ/molChydWilliams, 1942liquid phase; solvent: Acetic acid; Reanalyzed by Cox and Pilcher, 1970, Original value = -108.0 ± 8.5 kJ/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