Pyrene

• Formula: C₁₆H₁₀
• Molecular weight: 202.2506
• IUPAC Standard InChI: InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H Copy

  
• IUPAC Standard InChIKey: BBEAQIROQSPTKN-UHFFFAOYSA-N Copy
• CAS Registry Number: 129-00-0
• 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: β-Pyrene; Benzo[def]phenanthrene; Pyren; Coal tar pitch volatiles:pyrene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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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)
LL - Sharon G. Lias and Joel F. Liebman
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 C₁₆H₁₀⁺ (ion structure unspecified)

Electron affinity determinations

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

References

Go To: Top, 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.

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]

Ando, Kokubo, et al., 2004
Ando, N.; Kokubo, S.; Mitsui, M.; Nakajima, A., Photoelectron spectroscopy of pyrene cluster anions, (pyrene)(-)(n) (n=1-20), Chem. Phys. Lett., 2004, 389, 4-6, 279-283, https://doi.org/10.1016/j.cplett.2004.03.100 . [all data]

Wentworth and Becker, 1962
Wentworth, W.E.; Becker, R.S., Potential Method for the Determination of Electron Affinities of Molecules: Application to Some Aromatic Hydrocarbons., J. Am. Chem. Soc., 1962, 84, 22, 4263, https://doi.org/10.1021/ja00881a014 . [all data]

Lyons, Morris, et al., 1968
Lyons, L.E.; Morris, G.C.; Warren, L.J., Electron Affinities and the Electron Capture Method for Aromatic Hydrocarbons, J. Phys. Chem., 1968, 72, 10, 3677, https://doi.org/10.1021/j100856a056 . [all data]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [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]

Hager and Wallace, 1988
Hager, J.W.; Wallace, S.C., Two-laser photoionization supersonic jet mass spectrometry of aromatic molecules, Anal. Chem., 1988, 60, 5. [all data]

Clar, Robertson, et al., 1981
Clar, E.; Robertson, J.M.; Schlogl, R.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. 6. Application to structural elucidation: 'Circumanthracene', J. Am. Chem. Soc., 1981, 103, 1320. [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, 1979
Clar, E.; Schmidt, W., Correlations between photoelectron and UV absorption spectra of polycyclic hydrocarbons. The pyrene series, Tetrahedron, 1979, 35, 1027. [all data]

Dewar and Goodman, 1972
Dewar, M.J.S.; Goodman, D.W., Photoelectron spectra of molecules. Part 5.--Polycyclic aromatic hydrocarbons, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1784. [all data]

Wacks, 1964
Wacks, M.E., Electron-impact studies of aromatic hydrocarbons. II. Naphthacene, naphthaphene, chrysene, triphenylene, and pyrene, J. Chem. Phys., 1964, 41, 1661. [all data]

Kuroda, 1964
Kuroda, H., Ionization potentials of polycyclic aromatic hydrocarbons, Nature, 1964, 201, 1214. [all data]

Finch, 1964
Finch, A.C.M., Charge-transfer spectra and the ionization energy of azulene, J. Chem. Soc., 1964, 2272. [all data]

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

Kinoshita, 1962
Kinoshita, M., The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil, Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]

Briegleb, Czekalla, et al., 1961
Briegleb, G.; Czekalla, J.; Reuss, G., Mesomeriemomente und Elektronenuberfuhrungsbanden von Elektronen-donator-akzeptor-komplexen des Chloranils und Tetracyanathylens mit aromatischen Kohlenwasserstoffen, Z. Phys. Chem. (Neue Folge), 1961, 30, 333. [all data]

Birks and Stifkin, 1961
Birks, J.B.; Stifkin, M.A., π-Electronic excitation and ionization energies of condensed ring aromatic hydrocarbons, Nature, 1961, 191, 761. [all data]

Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J., Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen, Z.Elektrochem., 1959, 63, 6. [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]

Akiyama, Li, et al., 1979
Akiyama, I.; Li, K.C.; LeBreton, P.R.; Fu, P.P.; Harvey, R.G., Ultraviolet photoelectron studies of polycyclic aromatic hydrocarbons. The ground-state electronic structure of aryloxiranes and metabolites of benzo[a]pyrene, J. Phys. Chem., 1979, 83, 2997. [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]

Boschi and Schmidt, 1972
Boschi, R.; Schmidt, W., Photoelectron spectra of polycyclic aromatic hydrocarbons. Pyrene and coronene, Tetrahedron Lett., 1972, 25, 2577. [all data]

Notes

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

• Symbols used in this document:
  

  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy

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