2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-

• Formula: C₈H₈O₂
• Molecular weight: 136.1479
• IUPAC Standard InChI: InChI=1S/C8H8O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3 Copy

  
• IUPAC Standard InChIKey: MYKLQMNSFPAPLZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 137-18-8
• 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-Benzoquinone, 2,5-dimethyl-; p-Xyloquinone; Phlorone; 2,5-Dimethyl-p-benzoquinone; 2,5-Dimethyl-1,4-benzoquinone; 2,5-Dimethylquinone; 2,5-Xyloquinone; 3,6-Dimethyl-p-benzoquinone; Benzoquinone, 2, 5-dimethyl-; 2,5-Dimethyl-1,4-benzochinon; 2,5-Dimetilbenzochinone (1:4); Floron; Florone; 2,5-Dimethyl-2,5-Cyclohexadiene-1,4-dione; 2,5-Dimethyl-p-quinone; NSC 15309
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

View reactions leading to C₈H₈O₂⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (MINERAL OIL MULL); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLID (OIL MULL) $$SPECTRAL CONTAMINATION DUE TO OIL AROUND 2900 CM^-1; PERKIN-ELMER 21 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (5% CCl4 FOR 3800-1330, 5% CS2 FOR 1330-400); BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY (ADJUSTED subtractcm-1only3600); 2 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

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

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

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Coolidge and Coolidge, 1927
Coolidge, A.S.; Coolidge, M.S., The sublimation pressures of substituted quinones and hydroquinones, J. Am. Chem. Soc., 1927, 49, 100-104. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [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]

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]

Kobayashi, 1975
Kobayashi, T., Photoelectron spectra of p-benzoquinones, J. Electron. Spectrosc. Relat. Phenom., 1975, 7, 349. [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]

Cram and Reeves, 1958
Cram, D.J.; Reeves, R.A., Macro rings. XIV. Substitution studies in the [4.4]paracyclophane system, J. Am. Chem. Soc., 1958, 80, 3094-3103. [all data]

Hill, Isaacs, et al., 1999
Hill, V.M.; Isaacs, N.S.; Ledward, D.A.; Ames, J.M., Effect of high hydrostatic pressure on the volatile components of a glucose-lysine model system, J. Agric. Food Chem., 1999, 47, 9, 3675-3681, https://doi.org/10.1021/jf990124z . [all data]

Notes

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• Symbols used in this document:
  

  EA	Electron affinity
  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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