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
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, 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.

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]

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]

Swietoslawski and Starczedska, 1925
Swietoslawski, W.; Starczedska, H., Correction des donnees thermochimiques de M.A. Valeur, J. Chem. Phys., 1925, 22, 399-401. [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]

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]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid 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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