1,3,5-Cycloheptatriene
- Formula: C7H8
- Molecular weight: 92.1384
- IUPAC Standard InChIKey: CHVJITGCYZJHLR-UHFFFAOYSA-N
- CAS Registry Number: 544-25-2
- 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: Tropilidene; Cyclohepta-1,3,5-triene; Cycloheptatriene; Tropilidin; UN 2603
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Gas phase ion energetics data
Go To: Top, 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:
B - John E. Bartmess
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 C7H8+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.29 | PI | Traeger and McLoughlin, 1978 | LLK |
8.03 | PE | Traeger and McLoughlin, 1978 | LLK |
8.52 | EI | Hoffman, 1974 | LLK |
8.40 | PE | Bodor, Dewar, et al., 1970 | RDSH |
8.20 ± 0.05 | PI | Akopyan and Vilesov, 1966 | RDSH |
8.28 | S | Price, Passmore, et al., 1963 | RDSH |
8.50 | PE | Muller, Schweig, et al., 1974 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H5+ | 16.66 | ? | EI | Harrison, Haynes, et al., 1965 | RDSH |
C5H5+ | 16.0 | ? | EI | Lifshitz and Bauer, 1963 | RDSH |
C6H5+ | 14.17 | CH3 | EI | Hoffman, 1974 | LLK |
C7H7+ | 9.36 | H | PI | Traeger and McLoughlin, 1978 | LLK |
C7H7+ | 9.36 ± 0.02 | H | TE | Traeger and McLoughlin, 1977 | LLK |
C7H7+ | 10.73 | H | EI | Hoffman, 1974 | LLK |
C7H7+ | ≤10.0 | H | PI | Akopyan and Vilesov, 1966 | RDSH |
C7H7+ | 10.1 ± 0.2 | H | EI | Harrison, Honnen, et al., 1960 | RDSH |
De-protonation reactions
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 375.2 ± 2.2 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 369.2 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Traeger and McLoughlin, 1978
Traeger, J.C.; McLoughlin, R.G.,
A photoionization study of the energetics of C7H7+ ion formed from C7H8 precursors,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 319. [all data]
Hoffman, 1974
Hoffman, M.K.,
Hidden rearrangements in the mass spectral decomposition of cycloheptatriene,
Z. Naturforsch. A:, 1974, 29, 1077. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I.,
A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A,
Zh. Fiz. Khim., 1966, 40, 125, In original 63. [all data]
Price, Passmore, et al., 1963
Price, W.C.; Passmore, T.R.; Roessler, D.M.,
[Title unavailable],
Faraday Discuss. Chem. Soc., 1963, 35, 238. [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]
Harrison, Haynes, et al., 1965
Harrison, A.G.; Haynes, P.; McLean, S.; Meyer, F.,
The mass spectra of methyl-substituted cyclopentadienes,
J. Am. Chem. Soc., 1965, 87, 5099. [all data]
Lifshitz and Bauer, 1963
Lifshitz, C.; Bauer, S.H.,
Mass spectra of valence tautomers,
J. Phys. Chem., 1963, 67, 1629. [all data]
Traeger and McLoughlin, 1977
Traeger, J.C.; McLoughlin, R.G.,
Threshold photoionization and dissociation of toluene and cycloheptatriene,
J. Am. Chem. Soc., 1977, 99, 7351. [all data]
Harrison, Honnen, et al., 1960
Harrison, A.G.; Honnen, L.R.; Dauben, H.J., Jr.; Lossing, F.P.,
Free radicals by mass spectrometry. XX. Ionization potentials of cyclopentadienyl and cycloheptatrienyl radicals,
J. Am. Chem. Soc., 1960, 82, 5593. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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