Benzo[ghi]perylene

• Formula: C₂₂H₁₂
• Molecular weight: 276.3307
• IUPAC Standard InChI: InChI=1S/C22H12/c1-3-13-7-9-15-11-12-16-10-8-14-4-2-6-18-17(5-1)19(13)21(15)22(16)20(14)18/h1-12H Copy

  
• IUPAC Standard InChIKey: GYFAGKUZYNFMBN-UHFFFAOYSA-N Copy
• CAS Registry Number: 191-24-2
• 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: Benzo-1,12-perylene; 1,12-Benzoperylene; 1,12-Benzperylene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Phase change data

Go To: Top, Gas phase ion energetics data, Ion clustering 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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 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

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Ion clustering data

Go To: Top, Phase change 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 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

C₂₂H₁₂⁺ +  = (C₂₂H₁₂⁺ • )

By formula: C₂₂H₁₂⁺ + C₂₂H₁₂ = (C₂₂H₁₂⁺ • C₂₂H₁₂)

Bond type: Charge transfer bond (positive ion)

C₂₂H₁₃⁺ +  = (C₂₂H₁₃⁺ • )

By formula: C₂₂H₁₃⁺ + C₂₂H₁₂ = (C₂₂H₁₃⁺ • C₂₂H₁₂)

Free energy of reaction

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Smith, 1980
Smith, G.W., Phase behavior of some condensed polycyclic aromatics, Mol. Cryst. Liq. Cryst., 1980, 64, 15. [all data]

Casellato, Vecchi, et al., 1973
Casellato, F.; Vecchi, C.; Girell, A., Differential calorimetric study of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1973, 6, 4, 361, https://doi.org/10.1016/0040-6031(73)87003-0 . [all data]

Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S., Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons, J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x . [all data]

Wakayama and Inokuchi, 1967
Wakayama, N.; Inokuchi, H., Heats of sublimation of polycyclic aromatic hydrocarbons and their molecular packings, Bull. Chem. Soc. Jpn., 1967, 40, 2267. [all data]

Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank, Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons, J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148 . [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]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Murray, Pottie, et al., 1974
Murray, John James; Pottie, Roswell Francis; Pupp, Christian, The Vapor Pressures and Enthalpies of Sublimation of Five Polycyclic Aromatic Hydrocarbons, Can. J. Chem., 1974, 52, 4, 557-563, https://doi.org/10.1139/v74-087 . [all data]

Wakayama and Inokuchi, 1967, 2
Wakayama, Nobuko; Inokuchi, Hiroo, Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings, Bull. Chem. Soc. Jpn., 1967, 40, 10, 2267-2271, https://doi.org/10.1246/bcsj.40.2267 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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]

Clar and Schmidt, 1977
Clar, E.; Schmidt, W., Correlations between photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons. The perylene, coronene and bisanthene series, Tetrahedron, 1977, 33, 2093. [all data]

Boschi, Murrell, et al., 1972
Boschi, R.; Murrell, J.N.; Schmidt, W., Photoelectron spectra of polycyclic aromatic hydrocarbons, Faraday Discuss. Chem. Soc., 1972, 54, 116. [all data]

Briegleb, 1964
Briegleb, G., Electron affinity of organic molecules, Angew. Chem. Intern. Ed., 1964, 3, 617. [all data]

Matsen, 1956
Matsen, F.A., Electron affinities, methyl affinities, and ionization energies of condensed ring aromatic hydrocarbons, J. Chem. Phys., 1956, 24, 602. [all data]

Clar and Schmidt, 1976
Clar, E.; Schmidt, W., Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons, Tetrahedron, 1976, 32, 2563. [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, Phase change data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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