2,4,6-Cycloheptatrien-1-one, 2-hydroxy-

• Formula: C₇H₆O₂
• Molecular weight: 122.1213
• IUPAC Standard InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9) Copy

  
• IUPAC Standard InChIKey: MDYOLVRUBBJPFM-UHFFFAOYSA-N Copy
• CAS Registry Number: 533-75-5
• 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: Tropolone; Purpurocatechol; 2-Hydroxy-2,4,6-cycloheptatriene-1-one; 2-Hydroxy-2,4,6-cycloheptatrien-1-one; 2-hydroxycyclohepta-2,4,6-trienone
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • 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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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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:
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:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

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

Gas Phase Spectrum

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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, 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

Normal alkane RI, 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.

Hubbard, Katz, et al., 1952
Hubbard, W.N.; Katz, C.; Guthrie, G.B., Jr.; Waddington, G., The heat of combustion and resonance energy of tropolone, J. Am. Chem. Soc., 1952, 74, 4456-44. [all data]

Cook, Gibb, et al., 1951
Cook, J.W.; Gibb, A.R.; Raphael, R.A.; Somerville, A.R., Tropolones. Part I. The preparation and general characteristics of tropolone, J. Chem. Soc., 1951, 503-511. [all data]

Tanaka and Watase, 1956
Tanaka, T.; Watase, T., Resonance energies of tropolone and hinokitiol, Tech. Rpt., Osaka Univ., 1956, 6, 367-371. [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]

Jackson, Hung, et al., 1971
Jackson, W.; Hung, T.S.; Hopkins, H.P., Jr., Delocalization energies of troponoids from bomb calorimetric and vapour pressure measurements, J. Chem. Thermodyn., 1971, 3, 347-353. [all data]

Cook, Gibb, et al., 1951, 2
Cook, J.W.; Gibb, A.R.; Raphael, R.A.; Somerville, A.R., 107. Tropolones. Part I. The preparation and general characteristics of tropolone, J. Chem. Soc., 1951, 503, https://doi.org/10.1039/jr9510000503 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Higasi, Nozoe, et al., 1957
Higasi, K.; Nozoe, T.; Omura, I., Ionization potentials of some organic molecules. IV. Troponoid compounds, Bull. Chem. Soc. Japan, 1957, 30, 408. [all data]

Williams, Cooks, et al., 1968
Williams, D.H.; Cooks, R.G.; Howe, I., Studies in mass spectrometry. XXXI. A comparison of reaction rates in common ions generated via fragmentation and direct ionization, J. Am. Chem. Soc., 1968, 90, 6759. [all data]

Aulin-Erdtman and Forbes, 1967
Aulin-Erdtman, G.; Forbes, E.J., UV atlas of organic compounds, 1967, 3, F3/3. [all data]

Souza, Re-Poppi, et al., 2012
Souza, J.B.G.; Re-Poppi, N.; Raposo, J.L.(Jr)., Characterization of pyroligneous acid used in agriculture by gas chromatography - mass spectrometry (in press), J. Braz. Chem. Soc., 2012, 00, 00, 1-8. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  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
  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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