9,10-Anthracenedione

• Formula: C₁₄H₈O₂
• Molecular weight: 208.2121
• IUPAC Standard InChI: InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H Copy

  
• IUPAC Standard InChIKey: RZVHIXYEVGDQDX-UHFFFAOYSA-N Copy
• CAS Registry Number: 84-65-1
• 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: Anthraquinone; Anthradione; Hoelite; Morkit; 9,10-Anthraquinone; Anthracene, 9,10-dihydro-9,10-dioxo-; 9,10-Dioxoanthracene; 9,10-Anthrachinon; Corbit; Anthracene-9,10-quinone; NSC 7957; anthracene-9,10-dione; 9,10-anthracenequinone
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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:
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

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas Chromatography, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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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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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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]

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]

Burriel, 1931
Burriel, F., 7. Estudio fisico-quimico de algunos compuestos organicos solidos a la temperatura ordinaria, que se proponen como patrones de temperatura, An. R. Soc. Esp. Fis. Quim., 1931, 29, 89-125. [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]

Hildebrand, Duschak, et al., 1917
Hildebrand, J.H.; Duschak, A.D.; Foster, A.H., and Beebe, C.W. The specific heats and heats of fusion of triphenylmethane, anthraquinone and anthracene, J. Am. Chem. Soc., 1917, 39, 2293-2297. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Burriel, 1931, 2
Burriel, F., Physico-Chemical Study of Some Solid Organic Compounds at Ordinary Temperatures, and Their COrrelationo with Temperature, An. R. Soc. Esp. Fis. Quim., 1931, 29, 89. [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

NISHIDA, ISHIHARA, et al., 2008
NISHIDA, K.; ISHIHARA, E.; OSAKA, T.; KOUKITU, M., Vapour Pressures and Heats of Sublimation of Some Disperse Dyes, J Food Science, 2008, 93, 2, 52-54, https://doi.org/10.1111/j.1478-4408.1977.tb03324.x . [all data]

Nishida, Ishihara, et al., 1978
Nishida, K.; Ishihara, E.; Osaka, T.; Koukitu, M., Vapor pressures and heats of sublimation of some disperse dyes, Galaxia, 1978, 72, 13. [all data]

Bardi, Gigli, et al., 1973
Bardi, Giampiero; Gigli, Rosario; Malaspina, Leopoldo; Piacente, Vincenzo, Vapor pressure and sublimation enthalpy of anthraquinone and of 1,5- and 1,8-dihydroxyanthraquinones, J. Chem. Eng. Data, 1973, 18, 2, 126-130, https://doi.org/10.1021/je60057a024 . [all data]

Beech and Lintonbon, 1971
Beech, Graham; Lintonbon, Roger M., The measurement of sublimation enthalpies by differential scanning calorimetry, Thermochimica Acta, 1971, 2, 1, 86-88, https://doi.org/10.1016/0040-6031(71)85027-X . [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Inokuchi, Shiba, et al., 1952
Inokuchi, Hiroo; Shiba, Sukekuni; Handa, Takashi; Akamatu, Hideo, Heats of Sublimation of Condensed Polynuclear Aromatic Hydrocarbons, Bull. Chem. Soc. Jpn., 1952, 25, 5, 299-302, https://doi.org/10.1246/bcsj.25.299 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [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]

Zenkevich, 1994
Zenkevich, I.G., Contemporary State of Informational Maintenance for Gas Chromatographic Identification of Chlorinated Polycyclic Aromatic Compounds, Zh. Ecol. Khim., 1994, 3, 2, 111-119. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R., Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds., Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c . [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]

Blanco, Blanco, et al., 1989
Blanco, C.G.; Blanco, J.; Bermejo, J.; Guillen, M.D., Capillary gas chromatography of some polycyclic aromatic compounds on several stationary phases, J. Chromatogr., 1989, 465, 3, 378-385, https://doi.org/10.1016/S0021-9673(01)92675-5 . [all data]

König, Balfanz, et al., 1983
König, J.; Balfanz, E.; Funcke, W.; Romanowski, T., Determination of oxygenated polycyclic aromatic hydrocarbons in airborne particulate matter by capillary gas chromatography and gas chromatography/mass spectrometry, Anal. Chem., 1983, 55, 4, 599-603, https://doi.org/10.1021/ac00255a004 . [all data]

Lundstedt, Haglund, et al., 2003
Lundstedt, S.; Haglund, P.; Öberg, L., Degradation and formation of polycyclic aromatic compounds during bioslurry treatment of an aged gasworks soil, Environ. Toxicol. Chem., 2003, 22, 7, 1413-1420, https://doi.org/10.1002/etc.5620220701 . [all data]

Eckel, 2000
Eckel, W.P., Making sense of nontarget compound data from GC-MS library searches, Am. Lab. Fairfield Conn., 2000, 17-20. [all data]

Helmig and Harger, 1994
Helmig, D.; Harger, W.P., OH radical-initiated gas-phase reaction products of phenanthrene, Sci. Total Environ., 1994, 148, 1, 11-21, https://doi.org/10.1016/0048-9697(94)90368-9 . [all data]

Kelly, Bartle, et al., 1992
Kelly, G.W.; Bartle, K.D.; Clifford, A.A.; Robinson, R.E., Application of coupled LC-GC to the analysis of the polar fraction of diesel particulate matter, J. Hi. Res. Chromatogr., 1992, 15, 8, 526-530, https://doi.org/10.1002/jhrc.1240150808 . [all data]

Tucminen, Wickstrom, et al., 1986
Tucminen, A.; Wickstrom, K.; Pyysalo, H., Determination of Polycyclic Aromatic Compounds by GLC-Selected Ion Monitoring (SIM) Technique, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 469-471, https://doi.org/10.1002/jhrc.1240090813 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

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