2,4,6-Cycloheptatrien-1-one

• Formula: C₇H₆O
• Molecular weight: 106.1219
• IUPAC Standard InChI: InChI=1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H Copy

  
• IUPAC Standard InChIKey: QVWDCTQRORVHHT-UHFFFAOYSA-N Copy
• CAS Registry Number: 539-80-0
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Tropone; Cycloheptatrienone; Tropon; 2,4,6-Cycloheptatriene-1-one
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

3 +  =

By formula: 3H₂ + C₇H₆O = C₇H₁₂O

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:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₆O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

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

View large format table.

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes

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

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Ziesel, Malinovich, et al., 1987
Ziesel, Z.P.; Malinovich, Y.; Ohmichi, N.; Lifshitz, C., Time-dependent mass spectra and breakdown graphs: The decarbonylation of tropone, Chem. Phys. Lett., 1987, 136, 81. [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]

Allan, Heilbronner, et al., 1975
Allan, M.; Heilbronner, E.; Kloster-Jensen, E., A photoelectron-spectroscopic investigation of benzologue tropones, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 181. [all data]

Muller, Schweig, et al., 1974
Muller, C.; Schweig, A.; Vermeer, H., Methode zur Berechnung induktiver und konjugativer Effekte - Andwendung auf Tropon, Angew. Chem., 1974, 86, 275. [all data]

Bunzli, Frost, et al., 1974
Bunzli, J.C.; Frost, D.C.; Weiler, L., Photoelectron spectrum of tropone. Inductive effect of carbonyl group, J. Am. Chem. Soc., 1974, 96, 1952. [all data]

Dickschat J.S., Wagner-Dobler I., et al., 2005
Dickschat J.S.; Wagner-Dobler I.; Schulz S., The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria, J. Chem. Ecol., 2005, 31, 4, 925-947, https://doi.org/10.1007/s10886-005-3553-9 . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  ΔrH°	Enthalpy of reaction at standard conditions

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