2,4,6-Cycloheptatrien-1-one

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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

Quantity Value Units Method Reference Comment
Δcliquid-860.9 ± 0.8kcal/molCcbJackson, Hung, et al., 1971Corresponding Δfliquid = -2.4 kcal/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tfus268.KN/ATurner, Meador, et al., 1957Uncertainty assigned by TRC = 2. K; TRC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
386.20.020Weast and Grasselli, 1989BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
13.0288.AStephenson and Malanowski, 1987Based on data from 273. to 323. K.; AC
12.9 ± 0.1297.0 ± 0.5VJackson, Hung, et al., 1971ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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

3Hydrogen + 2,4,6-Cycloheptatrien-1-one = Cycloheptanone

By formula: 3H2 + C7H6O = C7H12O

Quantity Value Units Method Reference Comment
Δr-67.58 ± 0.30kcal/molChydTurner, Meador, et al., 1957, 2liquid phase; solvent: Acetic acid

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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)

Quantity Value Units Method Reference Comment
Proton affinity (review)220.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity213.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.88 ± 0.05TRPIZiesel, Malinovich, et al., 1987LBLHLM
9.68 ± 0.02EIHigasi, Nozoe, et al., 1957RDSH
8.89 ± 0.03PEAllan, Heilbronner, et al., 1975Vertical value; LLK
8.82PEMuller, Schweig, et al., 1974Vertical value; LLK
8.90 ± 0.02PEBunzli, Frost, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H6+9.58 ± 0.05COTRPIZiesel, Malinovich, et al., 1987LBLHLM

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, 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

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1994
NIST MS number 133315

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

UVVis spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Source Timmons and Ciabattoni, 1967
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 19838
Instrument Unicam SP 700

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

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]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W. vonE.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of Hydrogenation III. Hydrogenation of Cyclooctatetraene and of Some Seven-membered Non-benzenoid Aromatic Compounds, J. Am. Chem. Soc., 1957, 79, 4127. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Turner, Meador, et al., 1957, 2
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]

Timmons and Ciabattoni, 1967
Timmons, C.J.; Ciabattoni, J., UV atlas of organic compounds, 1967, 3, F3/2. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References