Biphenyl

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas43.1 ± 0.7kcal/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
12.0350.Dorofeeva O.V., 1997None of the statistically calculated values of S(T) known from literature [ Trevissoi C., 1955, Katon J.E., 1959, Aleman H., 1973, Thermodynamics Research Center, 1997] is in full accord with experimental data (see also discussion in [ Chirico R.D., 1989]). Recommended values agree with experimental values within their uncertainties except for temperature range 340-460 K where discrepancies amount to 0.4-0.6 J/mol*K.; GT
15.49100.
20.14150.
26.030200.
36.202273.15
39.84 ± 0.24298.15
40.105300.
53.903400.
65.397500.
74.517600.
81.773700.
87.655800.
92.512900.
96.5731000.
100.001100.
102.931200.
105.431300.
107.571400.
109.431500.

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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfsolid23.5 ± 0.60kcal/molReviewRoux, Temprado, et al., 2008There are sufficient high-quality literature values to make a good evaluation with a high degree of confidence. In general, the evaluated uncertainty limits are on the order of (0.5 to 2.5) kJ/mol.; DRB
Δfsolid23.12 ± 0.62kcal/molCcbMontgomery, Rossini, et al., 1978ALS
Δfsolid24.02 ± 0.36kcal/molCcbColeman and Pilcher, 1966ALS
Δfsolid23.14 ± 0.96kcal/molCcbMackle and O'Hare, 1963ALS
Δfsolid23.24 ± 0.39kcal/molCcbParks and Vaughan, 1951Reanalyzed by Cox and Pilcher, 1970, Original value = 23.10 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcsolid-1494. ± 5.kcal/molAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
solid,1 bar50.043cal/mol*KN/AChirico, Knipmeyer, et al., 1989DH
solid,1 bar49.952cal/mol*KN/ASaito, Atake, et al., 1988DH
solid,1 bar49.21cal/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 65.4 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
68.19370.Walker, Brooks, et al., 1958T = 200 to 600°F.; DH
71.99422.McEwen, March 31 1956T = 300 to 600°C.; DH
71.70370.Kurbatov, 1950T = 98 to 255°C. Mp 70.8°C.; DH
62.91350.8Forrest, Brugmann, et al., 1931T = 350 to 620 K. Value is unsmoothed experimental datum.; DH
62.032298.Newton, Kaura, et al., 1931T = 100 to 300°C, equation only, in t°C. Cp(liq) = 0.388 + 0.00057t cal/g*K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
47.416298.15Chirico, Knipmeyer, et al., 1989T = 5 to 700 K.; DH
47.364298.15Saito, Atake, et al., 1988T = 3 to 300 K.; DH
47.25298.15O'Rourke and Mraw, 1983T = 220 to 475 K. Cp = 0.7143 (T/K) - 15.3 (220 to 342.2 K) J/mol*K.; DH
45.4300.Wasicki, Radomska, et al., 1982T = 180 to 350 K. Data given graphically. Value estimated from graph.; DH
45.60298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
47.30298.1Schmidt, 1941T = 20 to 200°C, equations only, in t°C. Cp(c) = 0.2745 + 0.001235t cal/g*K (20 to 69°C); Cp(liq) = 0.3917 + 0.0005206t cal/g*K (69 to 200°C).; DH
47.30303.Spaght, Thomas, et al., 1932T = 30 to 100°C.; DH
46.39294.4Huffman, Parks, et al., 1930T = 93 to 295 K. Value is unsmoothed experimental datum.; DH

Reaction 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões
ALS - 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

C10H8+ + Biphenyl = (C10H8+ • Biphenyl)

By formula: C10H8+ + C12H10 = (C10H8+ • C12H10)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr13.5kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr28.cal/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
5.2297.PHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

C12H8+ + Biphenyl = (C12H8+ • Biphenyl)

By formula: C12H8+ + C12H10 = (C12H8+ • C12H10)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr13.4kcal/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr28.cal/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
5.5279.PHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated; M

C17H24F3N3O3RuS (solution) + Biphenyl (solution) = C23H25F3O3RuS (solution) + 3Acetonitrile (solution)

By formula: C17H24F3N3O3RuS (solution) + C12H10 (solution) = C23H25F3O3RuS (solution) + 3C2H3N (solution)

Quantity Value Units Method Reference Comment
Δr-3.61 ± 0.1kcal/molRSCNolan, Martin, et al., 1992solvent: Tetrahydrofuran; MS

3Hydrogen + Biphenyl = Benzene, cyclohexyl-

By formula: 3H2 + C12H10 = C12H16

Quantity Value Units Method Reference Comment
Δr-54.kcal/molEqkFrye, 1962liquid phase; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C12H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.16 ± 0.13eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)194.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity187.1kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.130 ± 0.035ECDWojnarovits and Foldiak, 1981EA is an upper limit: Chen and Wentworth, 1989. G3MP2B3 calculations indicate an EA of ca. -0.02 eV, anion unbound.; B

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
193.3Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
186.6Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.80 ± 0.05EILoudon and Mazengo, 1974LLK
8.9EIKoppel, Schwarz, et al., 1974LLK
7.95 ± 0.02PEMaier and Turner, 1972LLK
8.23 ± 0.01PEDewar, Haselbach, et al., 1970RDSH
8.20 ± 0.05PEEland and Danby, 1968RDSH
8.46CTSSlifkin and Allison, 1967RDSH
8.22 ± 0.15EIEland, Shepherd, et al., 1966RDSH
8.27 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
8.64CTSKinoshita, 1962RDSH
8.35CTSBriegleb, Czekalla, et al., 1961RDSH
8.4CTSBriegleb and Czekalla, 1959RDSH
8.39PEAkiyama, Li, et al., 1979Vertical value; LLK
8.34PERuscic, Kovac, et al., 1978Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4+18.1 ± 0.3?EINatalis and Franklin, 1965RDSH
C6H5+18.2 ± 0.5?EINatalis and Franklin, 1965RDSH
C7H5+20.9 ± 0.2?EINatalis and Franklin, 1965RDSH
C8H6+18.10 ± 0.05?EINatalis and Franklin, 1965RDSH
C9H7+16.08 ± 0.05?EINatalis and Franklin, 1965RDSH
C10H8+14.81 ± 0.05?EINatalis and Franklin, 1965RDSH
C11H7+14.8 ± 0.2CH3EILoudon and Mazengo, 1974LLK
C12H8+16.89 ± 0.08?EINatalis and Franklin, 1965RDSH
C12H9+13.6 ± 0.2HEILoudon and Mazengo, 1974LLK
C12H9+14.36HEINatalis and Franklin, 1965RDSH
C12H82+22.0 ± 1.0?EINatalis and Franklin, 1965RDSH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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.

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Trevissoi C., 1955
Trevissoi C., Specific heat and entropy of biphenyl, Ann. Chim. (Rome), 1955, 45, 943-959. [all data]

Katon J.E., 1959
Katon J.E., The vibrational spectra and geometrical configuration of biphenyl, Spectrochim. Acta, 1959, 15, 627-650. [all data]

Aleman H., 1973
Aleman H., Thermodynamic functions for biphenyl and the 4,4'-dihalogenobiphenyls, Thermochim. Acta, 1973, 7, 69-73. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Chirico R.D., 1989
Chirico R.D., The thermodynamic properties of biphenyl, J. Chem. Thermodyn., 1989, 21, 1307-1331. [all data]

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Montgomery, Rossini, et al., 1978
Montgomery, R.L.; Rossini, F.D.; Mansson, M., Enthalpies of combustion, vaporization, and formation of phenylbenzene, cyclohexylbenzene, and cyclohexylcyclohexane; enthalpy of hydrogenation of certain aromatic systems, J. Chem. Eng. Data, 1978, 23, 125-129. [all data]

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]

Mackle and O'Hare, 1963
Mackle, H.; O'Hare, P.A.G., A high-precision aneroid semi-micro combustion calorimeter, Trans. Faraday Soc., 1963, 59, 2693-2701. [all data]

Parks and Vaughan, 1951
Parks, G.S.; Vaughan, L.M., The heat of combustion of biphenyl, J. Am. Chem. Soc., 1951, 73, 2380-2381. [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]

Chirico, Knipmeyer, et al., 1989
Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Steele, W.V., The thermodynamic properties of biphenyl, J. Chem. Thermodyn., 1989, 21, 1307-1331. [all data]

Saito, Atake, et al., 1988
Saito, K.; Atake, T.; Chihara, H., Incommensurate phase transitions and anomalous lattice heat capacities of biphenyl, Bull. Chem. Soc. Japan, 1988, 61, 679-688. [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]

Walker, Brooks, et al., 1958
Walker, B.E., Jr.; Brooks, M.S.; Ewing, C.T.; Miller, R.R., Specific heat of biphenyl and other polyphenyls. Correlation of specific heat data for phenyl type compounds, J. Chem. Eng. Data, 1958, 3, 280-282. [all data]

McEwen, March 31 1956
McEwen, M., Preliminary engineering study of organic nuclear reactor coolant-moderators Monsanto Chemical Co, March 31 1956. [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]

Forrest, Brugmann, et al., 1931
Forrest, H.O.; Brugmann, E.W.; Cummings, L.W.T., The specific heat of diphenyl, Ind. Eng. Chem., 1931, 23, 37-39. [all data]

Newton, Kaura, et al., 1931
Newton, R.F.; Kaura, B.D.; DeVries, T., The specific heat of liquid diphenyl, Ind. Eng. Chem., 1931, 23, 35-37. [all data]

O'Rourke and Mraw, 1983
O'Rourke, D.F.; Mraw, S.C., Heat capacities and enthalpies of fusion of dibenzothiophene (220 to 560 K) and of biphenyl, cyclohexylbenzene, and cyclohexylcyclohexane (220 to 475 K). Enthalpies and temperatures of three transitions in solid cyclohexylcyclohexane, J. Chem. Thermodynam., 1983, 15, 489-502. [all data]

Wasicki, Radomska, et al., 1982
Wasicki, J.; Radomska, M.; Radomski, R., Heat capacities of diphenyl, p-terphenyl and p-quaterphenyl from 180 K to their melting points, J. Therm. Anal., 1982, 25, 509-514. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Schmidt, 1941
Schmidt, W.R., Thesis Washington University (St. Louis), 1941. [all data]

Spaght, Thomas, et al., 1932
Spaght, M.E.; Thomas, S.B.; Parks, G.S., Some heat capacity data on organic compounds obtained with a radiation calorimeter, J. Phys. Chem., 1932, 36, 882-888. [all data]

Meot-Ner (Mautner), 1980
Meot-Ner (Mautner), M., Dimer Cations of Polycyclic Aromatics: Experimental Bonding Energies and Resonance Stabilization, J. Phys. Chem., 1980, 84, 21, 2724, https://doi.org/10.1021/j100458a012 . [all data]

Nolan, Martin, et al., 1992
Nolan, S.P.; Martin, K.L.; Stevens, E.D.; Fagan, P., Organometallics, 1992, 11, 3947. [all data]

Frye, 1962
Frye, C.G., Equilibria in the hydrogenation of polycyclic aromatics, J. Chem. Eng. Data, 1962, 7, 592-595. [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]

Wojnarovits and Foldiak, 1981
Wojnarovits, L.; Foldiak, G., Electron capture detection of aromatic hydrocarbons, J. Chromatogr. Sci., 1981, 206, 511. [all data]

Chen and Wentworth, 1989
Chen, E.C.M.; Wentworth, W.E., Experimental Determination of Electron Affinities of Organic Molecules, Mol. Cryst. Liq. Cryst., 1989, 171, 271. [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z., Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds, Org. Mass Spectrom., 1974, 8, 179. [all data]

Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F., Elektronenstossinduzierte fragmentierung von acetylenverbindungen, Org. Mass Spectrom., 1974, 9, 324. [all data]

Maier and Turner, 1972
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls, Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]

Dewar, Haselbach, et al., 1970
Dewar, M.J.S.; Haselbach, E.; Worley, S.D., Calculated and observed ionization potentials of unsaturated polycyclic hydrocarbons; calculated heats of formation by several semiempirical s.c.f. m.o. methods, Proc. Roy. Soc. (London), 1970, A315, 431. [all data]

Eland and Danby, 1968
Eland, J.H.D.; Danby, C.J., Inner ionization potentials of aromatic compounds, Z. Naturforsch., 1968, 23a, 355. [all data]

Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [all data]

Eland, Shepherd, et al., 1966
Eland, J.H.D.; Shepherd, P.J.; Danby, C.J., Ionization potentials of aromatic molecules determined by analytical interpretation of electron impact data, Z. Naturforsch., 1966, 21a, 1580. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Briegleb, Czekalla, et al., 1961
Briegleb, G.; Czekalla, J.; Reuss, G., Mesomeriemomente und Elektronenuberfuhrungsbanden von Elektronen-donator-akzeptor-komplexen des Chloranils und Tetracyanathylens mit aromatischen Kohlenwasserstoffen, Z. Phys. Chem. (Neue Folge), 1961, 30, 333. [all data]

Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J., Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen, Z.Elektrochem., 1959, 63, 6. [all data]

Akiyama, Li, et al., 1979
Akiyama, I.; Li, K.C.; LeBreton, P.R.; Fu, P.P.; Harvey, R.G., Ultraviolet photoelectron studies of polycyclic aromatic hydrocarbons. The ground-state electronic structure of aryloxiranes and metabolites of benzo[a]pyrene, J. Phys. Chem., 1979, 83, 2997. [all data]

Ruscic, Kovac, et al., 1978
Ruscic, B.; Kovac, B.; Klasinc, L.; Gusten, H., Photoelectron spectroscopy of J. Heterocycl. Chem.. Fluorene analogues, Z. Naturforsch. A:, 1978, 33, 1006. [all data]

Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L., Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. I. Biphenyl, diphenylacetylene, and phenanthrene, J. Phys. Chem., 1965, 69, 2935. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References