1,4-Naphthalenedione

• Formula: C₁₀H₆O₂
• Molecular weight: 158.1534
• IUPAC Standard InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H Copy

  
• IUPAC Standard InChIKey: FRASJONUBLZVQX-UHFFFAOYSA-N Copy
• CAS Registry Number: 130-15-4
• 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: 1,4-Naphthoquinone; α-Naphthoquinone; p-Naphthoquinone; 1,4-Dihydro-1,4-diketonaphthalene; 1,4-Naphthylquinone; 1,4-Naphthaquinone; USAF CY-10; 1,4-Naftochinon; Rcra waste number U166; NSC 9583; Naphthoquinone
• 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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase ion energetics data

Go To: Top, 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:
L - Sharon G. Lias

Data compiled as indicated in comments:
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

Electron affinity determinations

Ionization energy determinations

Appearance 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.

Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A^- + B = A + B^-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO₂) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P., Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements, J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015 . [all data]

Chen and Wentworth, 1983
Chen, E.C.M.; Wentworth, W.E., Determination of molecular electron affinities using the electron capture detector in the pulse sampling mode at steady state, J. Phys. Chem., 1983, 87, 45. [all data]

Collins, Christophorou, et al., 1970
Collins, P.M.; Christophorou, L.G.; Chaney, E.L.; Carter, J.G., Energy Dependence of the Electron Attachment Cross Section and the Transient Negative Ion Lifetime for p-Benzoquinone and 1,4-naphthoquinone, Chem. Phys. Lett., 1970, 4, 10, 646, https://doi.org/10.1016/0009-2614(70)80108-7 . [all data]

Millefiori, Gulino, et al., 1990
Millefiori, S.; Gulino, A.; Casarin, M., UV Photoelectron spectra, reduction potentials and MO calculations of intramolecularly hydrogen-bonded naphtoquinones, J. Chim. Phys., 1990, 87, 317. [all data]

Redchenko, Freimanis, et al., 1980
Redchenko, V.V.; Freimanis, Y.F.; Dregeris, Y.Y., Photoelectron Spectroscopy of 2,3-Disubtituted naphthoquinones, J. Gen. Chem. USSR, 1980, 50, 1507, In original 1847. [all data]

Lauer, Schafer, et al., 1975
Lauer, G.; Schafer, W.; Schweig, A., Assignment of the four lowest ionized states of p-benzoquinone and the question of "lone pair" splitting in this system, Chem. Phys. Lett., 1975, 33, 312. [all data]

Potapov and Sorokin, 1971
Potapov, V.K.; Sorokin, V.V., Photoionization and ion-molecule reactions in quinones and alcohols, High Energy Chem., 1971, 5, 435, In original 487. [all data]

Grutzmacher and Lohmann, 1967
Grutzmacher, H.-F.; Lohmann, J., Massenspektrometrie instabiler organischer Molekule. I. Ionisations-potential und Bildungsenthalpie von Dehydrobenzol, Ann. Chem., 1967, 705, 81. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.