2,4,6-Cycloheptatrien-1-one
- Formula: C7H6O
- Molecular weight: 106.1219
- IUPAC Standard InChIKey: QVWDCTQRORVHHT-UHFFFAOYSA-N
- 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
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -860.9 ± 0.8 | kcal/mol | Ccb | Jackson, Hung, et al., 1971 | Corresponding ΔfHºliquid = -2.4 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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:
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 |
---|---|---|---|---|---|
Tfus | 268. | K | N/A | Turner, Meador, et al., 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
386.2 | 0.020 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.0 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 323. K.; AC |
12.9 ± 0.1 | 297.0 ± 0.5 | V | Jackson, Hung, et al., 1971 | ALS |
Reaction 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
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
By formula: 3H2 + C7H6O = C7H12O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -67.58 ± 0.30 | kcal/mol | Chyd | Turner, Meador, et al., 1957, 2 | liquid phase; solvent: Acetic acid |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 220.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 213.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.88 ± 0.05 | TRPI | Ziesel, Malinovich, et al., 1987 | LBLHLM |
9.68 ± 0.02 | EI | Higasi, Nozoe, et al., 1957 | RDSH |
8.89 ± 0.03 | PE | Allan, Heilbronner, et al., 1975 | Vertical value; LLK |
8.82 | PE | Muller, Schweig, et al., 1974 | Vertical value; LLK |
8.90 ± 0.02 | PE | Bunzli, Frost, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H6+ | 9.58 ± 0.05 | CO | TRPI | Ziesel, Malinovich, et al., 1987 | LBLHLM |
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.
Spectrum
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Additional Data
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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, 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, UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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