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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

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
Tboil556. ± 5.KAVGN/AAverage of 23 out of 24 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus325. ± 1.KAVGN/AAverage of 189 out of 195 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple324.340KN/AMesserly, Finke, et al., 1988, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltasub91.5 ± 0.7kJ/molBOsborn and Scott, 1980AC
Deltasub91.38 ± 0.46kJ/molVMorawetz, 1972ALS
Deltasub91.4 ± 0.5kJ/molCMorawetz, 1972, 2AC
Deltasub84.1kJ/molN/AColeman and Pilcher, 1966DRB
Deltasub73.2 ± 0.8kJ/molVWolf and Weghofer, 1938ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
67.4398.GCLei, Chankalal, et al., 2002Based on data from 323. - 473. K.; AC
64.1373.N/ASasse, N'guimbi, et al., 1989Based on data from 333. - 413. K.; AC
67.53 ± 0.10324.4VMesserly, Finke, et al., 1988, 2ALS
66.2 ± 0.2340.N/AMesserly, Finke, et al., 1988AC
57.374.AStephenson and Malanowski, 1987Based on data from 359. - 557. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
360.0 - 557.4.860972572.151-27.406Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
92.9308.EMSasse, N'guimbi, et al., 1989Based on data from 293. - 323. K.; AC
91.2 ± 0.4295.N/AKratt, Beckhaus, et al., 1983Based on data from 273. - 318. K.; AC
83.97 ± 0.46326.2VAihara, 1959crystal phase; ALS
84.1 ± 0.4286. - 307.VAihara, 1959, 2See also Cox and Pilcher, 1970, 2.; AC
72.4 ± 1.3304.MEBloink, Pausacker, et al., 1951Based on data from 290. - 317. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
22.73324.3Domalski and Hearing, 1996AC
23.010324.4Schmidt, 1941DH
22.573324.3Ferry and Thomas, 1933DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
70.9324.4Schmidt, 1941DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
8.23273.2Domalski and Hearing, 1996CAL
70.09324.3

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
2.24755273.150crystaline, IIcrystaline, IMesserly, Finke, et al., 1988DH
22.73052324.348crystaline, IliquidMesserly, Finke, et al., 1988DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
8.23273.150crystaline, IIcrystaline, IMesserly, Finke, et al., 1988DH
70.08324.348crystaline, IliquidMesserly, Finke, et al., 1988DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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)801.8kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity774.1kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.00 ± 0.05EIPignataro, Mancini, et al., 1972LLK
8.7 ± 0.1EIMcLafferty, Wachs, et al., 1970RDSH
9.1PEPignataro, Mancini, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+10.6C7H7EIMcLafferty, Wachs, et al., 1970RDSH

IR Spectrum

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, 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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Lang (editor), 1969
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19068
Instrument Beckman DU
Melting point 52

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

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 «pi»-systems, Chem. Commun., 1971, 142. [all data]

Lang (editor), 1969
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1969, 12, 135. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References