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 ion energetics data
Go To: Top, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 848.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.2 | kJ/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 (kJ/mol) | Reference | Comment |
---|---|---|
845.2 | 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) (kJ/mol) | Reference | Comment |
---|---|---|
819.2 | 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 |
Ion clustering data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering 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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase ion energetics data, Ion clustering data, UV/Visible spectrum, Gas Chromatography, 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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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 | Chemical Concepts |
NIST MS number | 190117 |
UV/Visible spectrum
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, 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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Download spectrum in JCAMP-DX format.
Source | missing citation |
---|---|
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. 9010 |
Instrument | Unicam SP 700 |
Melting point | 107-111 |
Gas Chromatography
Go To: Top, Gas phase ion energetics data, Ion clustering data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 248.9 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | HP-5 | 249.1 | Shao, Wang, et al., 2006 | 30. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
Capillary | SPB-5 | 249.2 | Knobloch and Engewald, 1993 | 40. C @ 2. min, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 240. | Aracil, Font, et al., 2005 | Column length: 60. m; Column diameter: 0.25 mm; Program: not specified |
Capillary | HP-5MS | 244.96 | Cheng, Liu, et al., 2005 | 30. m/0.30 mm/0.25 μm, He; Program: 50 0C (2 min) 8 0C/min -> 120 0C (3 min) 10 0C/min -> 230 0C |
References
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
Chem. Anal., 2007, 52, 141-156. [all data]
Shao, Wang, et al., 2006
Shao, X.; Wang, G.; Sun, Y.; Zhang, R.; Xie, K.; Liu, H.,
Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MS,
J. Chromatogr. Sci., 2006, 44, 3, 141-147, https://doi.org/10.1093/chromsci/44.3.141
. [all data]
Knobloch and Engewald, 1993
Knobloch, T.; Engewald, W.,
Identification of some polar polycyclic compounds in emissions from brown-coal-fired residential stoves,
J. Hi. Res. Chromatogr., 1993, 16, 4, 239-242, https://doi.org/10.1002/jhrc.1240160407
. [all data]
Aracil, Font, et al., 2005
Aracil, I.; Font, R.; Conesa, J.A.,
Semivolatile and volatile compounds from the pyrolysis and combustion of polyvinyl chloride,
J. Anal. Appl. Pyrolysis, 2005, 74, 1-2, 465-478, https://doi.org/10.1016/j.jaap.2004.09.008
. [all data]
Cheng, Liu, et al., 2005
Cheng, D.-X.; Liu, B.-X.; Sun, Y.-A.; Xie, B.; Zhang, H.-L.,
rapid analysis of pyrolysis products of cholesterol by GC-MS assited with boiling point - Lee retention index,
journal of Instrumental Analysis - Fenxi ceshi xuebao, 2005, 24, 6, 85-88. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature 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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