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
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• 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
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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

Enthalpy of sublimation

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:
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

Mass spectrum (electron ionization)

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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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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 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

Gas Chromatography

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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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

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

Ribeiro Da Silva, Ribeiro Da Silva, et al., 1989
Ribeiro Da Silva, M.A.V.; Ribeiro Da Silva, D.M.C.; Teixeira, J.A.S., Enthalpies of combustion of 1,4-naphthoquinone, 9,10-anthraquinone, 9,10-phenanthraquinone, 1,4,9,10-anthradiquinone, 5,8-dihydroxy-1,4-naphthoquinone, and 1,4-dihydroxy-9,10-anthraquinone, J. Chem. Thermodyn., 1989, 21, 265-274. [all data]

Singh S.N., 1969
Singh S.N., Thermodynamic properties of some condensed ring quinones, Indian J. Pure Appl. Phys., 1969, 7, 52-53. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Schmitt and Reid, 1986
Schmitt, W.J.; Reid, R.C., Solubility of Monofunctional Organic Solids in Chemical Diverse Supercritical Fluids, J. Chem. Eng. Data, 1986, 31, 204. [all data]

Magnus, 1956
Magnus, A., Die resonanzenergien der parachinone Aui grund der prazisionsmessungsen ihrer verbrennungswarmen durch herrn gerhard wittwer, Z. Phys. Chem. (Neue Folge), 1956, 9, 141-161. [all data]

de Kruif, 1981
de Kruif, C.G., Thermodynamic properties of 1,4-benzoquinone (BQ), 1,4-hydroquinone (HQ), 1,4-naphthoquinone (NQ), 1,4-naphthohydroquinone (NHQ), and the complexes BQ--HQ 1:1, NQ--HQ 1:1, NQ--NHQ 2:1, and NQ--NHQ 1:1, J. Chem. Phys., 1981, 74, 10, 5838, https://doi.org/10.1063/1.440898 . [all data]

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]

Kuboyama, 1960
Kuboyama, A., The n-π* transition band of acenaphthenequinone, Bull. Chem. Soc. Jpn., 1960, 33, 8, 1027-1030. [all data]

Llobera and García-Raso, 1987
Llobera, A.; García-Raso, A., Gas chromatographic behaviour of several p-quinones, J. Chromatogr., 1987, 393, 2, 305-311, https://doi.org/10.1016/S0021-9673(01)94227-X . [all data]

Oda, Yasuhara, et al., 1998
Oda, J.; Yasuhara, A.; Matsunaga, K.; Saito, Y., Identification of polycyclic aromatic hydrocarbons of the particulate accumulated in the tunnel duct of freeway and generation of their oxygenated derivatives, Jpn. J. Toxicol. Environ. Health, 1998, 44, 5, 334-351, https://doi.org/10.1248/jhs1956.44.334 . [all data]

Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W., Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [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]

Boenke and Ballschmiter, 1987
Boenke, A.; Ballschmiter, K., Fused quinones as retention index marker in high resolution gas chromatography with electron-capture detection (HRGC/ECD) of oxidized aromatic compounds, Fresenius J. Anal. Chem., 1987, 327, 1, 44-45, https://doi.org/10.1007/BF00474554 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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