Biphenylene
- Formula: C12H8
- Molecular weight: 152.1919
- IUPAC Standard InChIKey: IFVTZJHWGZSXFD-UHFFFAOYSA-N
- CAS Registry Number: 259-79-0
- 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: Cyclobutadibenzene; Diphenylene; 1,1'-Biphenylene; Dibenzocyclobutadiene
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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:
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 |
---|---|---|---|---|---|
ΔfH°gas | 417.2 ± 1.9 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There 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 |
ΔfH°gas | 420.4 ± 1.9 | kJ/mol | Ccb | Douslin, Scott, et al., 1976 | see Good, 1978; ALS |
ΔfH°gas | 440.0 | kJ/mol | N/A | Bedford, Carey, et al., 1962 | Value 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 |
---|---|---|---|
43.33 | 50. | Thermodynamics Research Center, 1997 | p=1 bar.; GT |
62.32 | 100. | ||
82.59 | 150. | ||
106.22 | 200. | ||
145.50 | 273.15 | ||
159.30 | 298.15 | ||
160.32 | 300. | ||
212.3 | 400. | ||
255.7 | 500. | ||
290.4 | 600. | ||
318.0 | 700. | ||
340.4 | 800. | ||
358.8 | 900. | ||
374.0 | 1000. | ||
386.9 | 1100. | ||
398.0 | 1200. | ||
407.0 | 1300. | ||
415.0 | 1400. | ||
422.0 | 1500. |
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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 333.4 ± 1.8 | kJ/mol | Review | Roux, Temprado, et al., 2008 | There 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 |
ΔfH°solid | 333.4 ± 1.1 | kJ/mol | Ccb | Douslin, Scott, et al., 1976 | crystal phase; see Good, 1978; ALS |
ΔfH°solid | 353. | kJ/mol | Ccb | Bedford, Carey, et al., 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6198.85 ± 0.92 | kJ/mol | Ccb | Douslin, Scott, et al., 1976 | crystal phase; see Good, 1978; Corresponding ΔfHºsolid = 333.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6219. ± 3. | kJ/mol | Ccb | Bedford, Carey, et al., 1962 | Corresponding ΔfHºsolid = 353. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -6198. ± 10. | kJ/mol | Ccb | Cass, Springall, et al., 1955 | Corresponding ΔfHºsolid = 333. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
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: 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
By formula: C10H8+ + C12H8 = (C10H8+ • C12H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.5 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
30. | 309. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
By formula: C12H9+ + C12H8 = (C12H9+ • C12H8)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrS° | 120. | J/mol*K | N/A | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
ΔrS° | 120. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1980 | gas phase |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
25. | 277. | PHPMS | Meot-Ner (Mautner), 1980 | gas phase; Entropy change calculated or estimated |
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.
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]
Cass, Springall, et al., 1955
Cass, R.C.; Springall, H.D.; Quincey, P.G.,
Heats of combustion and molecular structure. Part III. Diphenylene,
J. Chem. Soc., 1955, 1188-1190. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas T Temperature 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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