Biphenylene

Formula: C₁₂H₈
Molecular weight: 152.1919
IUPAC Standard InChI: InChI=1S/C12H8/c1-2-6-10-9(5-1)11-7-3-4-8-12(10)11/h1-8H
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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Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
- NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

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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
Δ_fH°_gas	99.71 ± 0.45	kcal/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
Δ_fH°_gas	100.48 ± 0.46	kcal/mol	Ccb	Douslin, Scott, et al., 1976	see Good, 1978; ALS
Δ_fH°_gas	105.2	kcal/mol	N/A	Bedford, Carey, et al., 1962	Value computed using Δ_fH_solid° value of 353.0 kj/mol from Bedford, Carey, et al., 1962 and Δ_subH° value of 87.0 kj/mol from Douslin, Scott, et al., 1976.; DRB

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
10.36	50.	Thermodynamics Research Center, 1997	p=1 bar.; GT
14.89	100.
19.74	150.
25.387	200.
34.775	273.15
38.074	298.15
38.317	300.
50.74	400.
61.11	500.
69.41	600.
76.00	700.
81.36	800.
85.76	900.
89.39	1000.
92.47	1100.
95.12	1200.
97.28	1300.
99.19	1400.
100.9	1500.

Condensed phase thermochemistry data

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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
Δ_fH°_solid	79.68 ± 0.43	kcal/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
Δ_fH°_solid	79.68 ± 0.26	kcal/mol	Ccb	Douslin, Scott, et al., 1976	crystal phase; see Good, 1978; ALS
Δ_fH°_solid	84.4	kcal/mol	Ccb	Bedford, Carey, et al., 1962	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1481.56 ± 0.22	kcal/mol	Ccb	Douslin, Scott, et al., 1976	crystal phase; see Good, 1978; Corresponding Δ_fHº_solid = 79.69 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1486.3 ± 0.7	kcal/mol	Ccb	Bedford, Carey, et al., 1962	Corresponding Δ_fHº_solid = 84.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1481.4 ± 2.5	kcal/mol	Ccb	Cass, Springall, et al., 1955	Corresponding Δ_fHº_solid = 79.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_fus	384.4	K	N/A	Yokozeki, Wilcox, et al., 1974	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	22. ± 8.	kcal/mol	AVG	N/A	Average of 6 values; Individual data points

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
19.8	383.	GS	Nass, Lenoir, et al., 1995	Based on data from 313. to 453. K.; AC
16.4 ± 0.2	295.	V	Wolf and Weghofer, 1938	ALS

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:

Gas phase ion energetics data

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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 ± 0.03	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	202.7	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	195.8	kcal/mol	N/A	Hunter and Lias, 1998	HL

Electron affinity determinations

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

Proton affinity at 298K

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

Gas basicity at 298K

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

Ionization energy determinations

IE (eV)	Method	Reference	Comment
7.56 ± 0.05	EQ	Mautner(Meot-Ner), 1980	LLK
7.61 ± 0.04	PE	Boschi, Clar, et al., 1974	LLK
7.53 ± 0.05	PE	Eland, 1972	LLK
7.56 ± 0.05	PE	Eland, 1969	RDSH
7.61	PE	Dewar and Tien, 1985	Vertical value; LBLHLM
7.60 ± 0.02	PE	Maier and Turner, 1972	Vertical value; LLK

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes

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]

Yokozeki, Wilcox, et al., 1974
Yokozeki, A.; Wilcox, C.F.; Bauer, S.H., Biphenylene. Internuclear Distances and Their Root Mean Square Amplitudes of Vibration, J. Am. Chem. Soc., 1974, 96, 1026. [all data]

Nass, Lenoir, et al., 1995
Nass, Karen; Lenoir, Dieter; Kettrup, Antonius, Calculation of the Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons by an Incremental Procedure, Angew. Chem. Int. Ed. Engl., 1995, 34, 16, 1735-1736, https://doi.org/10.1002/anie.199517351 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
EA	Electron affinity
IE (evaluated)	Recommended ionization energy
T_fus	Fusion (melting) point
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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