p-Benzoquinone, 2,3,5,6-tetrachloro-

• Formula: C₆Cl₄O₂
• Molecular weight: 245.875
• IUPAC Standard InChI: InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 Copy

  
• IUPAC Standard InChIKey: UGNWTBMOAKPKBL-UHFFFAOYSA-N Copy
• CAS Registry Number: 118-75-2
• 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: p-Chloranil; 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrachloro-; α-Chloranil; Chloranil; Coversan; Dow Seed Disinfectant No. 5; ENT 3,797; Khloranil; Psorisan; Quinone Tetrachloride; Reranil; Spergon; Spergon I; Spergon Technical; Tetrachloro-p-benzoquinone; Tetrachloro-p-quinone; Tetrachloro-1,4-benzoquinone; Tetrachlorobenzoquinone; Tetrachloroquinone; Vulklor; 2,3,5,6-Tetrachloro-p-benzoquinone; 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzoquinone; 2,3,5,6-Tetrachloroquinone; 2,3,5,6-Tetrachloro-2,5-cyclohexadiene-1,4-dione; G-444E; G-25804; Geigy-444e; Tetrachloroparabenzoquinone; 1,4-Benzoquinone, 2,3,5,6-tetrachloro-; Tetrachlorquinone; ENT 3797; NSC 8432
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Condensed phase thermochemistry data

Go To: Top, Gas phase ion energetics 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 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

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry 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 as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

References

Go To: Top, Condensed phase thermochemistry 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.

Sjostrom, 1936
Sjostrom, Av.G., De klorsubstituerade kinonernas och hydrokinonernas termokemi, Svensk. Kim. Tidr., 1936, 48, 121-124. [all data]

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Chihara and Masukane, 1973
Chihara, H.; Masukane, K., Heat capacity of solid tetrachloro-p-benzoquinone(chloranil) between 11 and 300K. Phase transitions at 92K, J. Chem. Phys., 1973, 59, 5397-5403. [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]

Brinkman, Gunther, et al., 1994
Brinkman, E.A.; Gunther, E.; Schafer, O.; Brauman, J.I., Bound Excited Electronic States of Anions, J. Chem. Phys., 1994, 100, 3, 1840, https://doi.org/10.1063/1.466535 . [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]

Cooper, Frey, et al., 1978
Cooper, C.D.; Frey, W.F.; Compton, R.N., Negative ion properties of fluoranil, chloranil, and bromanil: Electron affinities, J. Chem. Phys., 1978, 69, 2367. [all data]

Farragher and Page, 1966
Farragher, A.L.; Page, F.M., Experimental Determination of Electron Affinities. Part 9. - Benzoquinone, Chloranil and Related Compounds, Trans. Farad. Soc., 1966, 62, 3072, https://doi.org/10.1039/tf9666203072 . [all data]

Sato, Seki, et al., 1981
Sato, N.; Seki, K.; Inokuchi, H., Polarization energies of organic solids determined by ultraviolet photoelectron spectroscopy, J. Chem. Soc. Faraday Trans. 2, 1981, 77, 1621. [all data]

Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones, J. Am. Chem. Soc., 1977, 99, 3234. [all data]

Notes

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

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions

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