Biphenylene

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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:
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
Δfgas417.2 ± 1.9kJ/molReviewRoux, Temprado, et al., 2008There are sufficient literature values to make a qualified recommendation where the suggested value is in good agreement with values predicted using thermochemical cycles or from reliable estimates. In general, the evaluated uncertainty limits are on the order of (2 to 4) kJ/mol.; DRB
Δfgas420.4 ± 1.9kJ/molCcbDouslin, Scott, et al., 1976see Good, 1978; ALS
Δfgas440.0kJ/molN/ABedford, Carey, et al., 1962Value computed using ΔfHsolid° value of 353.0 kj/mol from Bedford, Carey, et al., 1962 and ΔsubH° value of 87.0 kj/mol from Douslin, Scott, et al., 1976.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
43.3350.Thermodynamics Research Center, 1997p=1 bar.; GT
62.32100.
82.59150.
106.22200.
145.50273.15
159.30298.15
160.32300.
212.3400.
255.7500.
290.4600.
318.0700.
340.4800.
358.8900.
374.01000.
386.91100.
398.01200.
407.01300.
415.01400.
422.01500.

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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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+ + Biphenylene = (C10H8+ • Biphenylene)

By formula: C10H8+ + C12H8 = (C10H8+ • C12H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr66.5kJ/molPHPMSMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Δr120.J/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated

Free energy of reaction

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

C12H9+ + Biphenylene = (C12H9+ • Biphenylene)

By formula: C12H9+ + C12H8 = (C12H9+ • C12H8)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr120.J/mol*KN/AMeot-Ner (Mautner), 1980gas phase; Entropy change calculated or estimated
Δr120.J/mol*KPHPMSMeot-Ner (Mautner), 1980gas phase

Free energy of reaction

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

Gas phase ion energetics 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 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)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C12H8+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)7.58 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)848.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity819.2kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.89 ± 0.10CIDCChen and Cooks, 1995B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
845.2Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
819.2Aue, 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
7.56 ± 0.05EQMautner(Meot-Ner), 1980LLK
7.61 ± 0.04PEBoschi, Clar, et al., 1974LLK
7.53 ± 0.05PEEland, 1972LLK
7.56 ± 0.05PEEland, 1969RDSH
7.61PEDewar and Tien, 1985Vertical value; LBLHLM
7.60 ± 0.02PEMaier and Turner, 1972Vertical value; LLK

References

Go To: Top, Gas 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.

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]

Douslin, Scott, et al., 1976
Douslin, D.R.; Scott, D.W.; Good, W.D.; Osborn, A.G., Thermodynamic properties of organic compounds and thermodynamic properties of fluids, Gov. Rep. Announce. Index U.S., 1976, 76, 97. [all data]

Good, 1978
Good, W.D., The enthalpies of formation of some bridged-ring polynuclear aromatic hydrocarbons, J. Chem. Thermodyn., 1978, 10, 553-558. [all data]

Bedford, Carey, et al., 1962
Bedford, A.F.; Carey, J.G.; Millar, I.T.; Mortimer, C.T.; Springall, H.D., Heats of combustion and molecular structure. Part VIII. Biphenylene, J. Chem. Soc., 1962, 3895-3898. [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]

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]

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]

Chen and Cooks, 1995
Chen, G.D.; Cooks, R.G., Electron affinities of polycyclic aromatic hydrocarbons determined by the kinetic method, J. Mass Spectrom., 1995, 30, 8, 1167, https://doi.org/10.1002/jms.1190300814 . [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]

Mautner(Meot-Ner), 1980
Mautner(Meot-Ner), M., Ion thermochemistry of low volatility compounds in the gas phase. 3. Polycyclic aromatics: Ionization energies, proton, and hydrogen affinities. Extrapolations to graphite, J. Phys. Chem., 1980, 84, 2716. [all data]

Boschi, Clar, et al., 1974
Boschi, R.; Clar, E.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons, J. Chem. Phys., 1974, 60, 4406. [all data]

Eland, 1972
Eland, J.H.D., Photoelectron spectra and ionization potentials of aromatic hydrocarbons, Int. J. Mass Spectrom. Ion Phys., 1972, 9, 214. [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Dewar and Tien, 1985
Dewar, M.J.S.; Tien, T.-P., Photoelectron spectrum of benzyne, J. Chem. Soc., Chem. Commun., 1985, 1243. [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]


Notes

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