7-Methylcycloheptatriene
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChI: InChI=1S/C8H10/c1-8-6-4-2-3-5-7-8/h2-8H,1H3
- IUPAC Standard InChIKey: OQWAEQHNVGGBHL-UHFFFAOYSA-N
- CAS Registry Number: 4281-04-3
- Chemical structure:
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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
ALS - 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
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 371.0 ± 2.5 | kcal/mol | G+TS | Mishima, Kinoshita, et al., 2002 | gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 363.3 ± 2.0 | kcal/mol | IMRE | Mishima, Kinoshita, et al., 2002 | gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB; B |
=
By formula: C8H10 = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.06 ± 0.07 | kcal/mol | Eqk | Egger, 1968 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C8H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.4 ± 0.1 | EI | Meyer, Haynes, et al., 1965 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7H7+ | 10.0 ± 0.1 | CH3 | EI | Meyer, Haynes, et al., 1965 | RDSH |
| C7H7+ | 9.5 ± 0.2 | CH3 | EI | Harrison, Honnen, et al., 1960 | RDSH |
| C8H9+ | 11.0 ± 0.1 | H | EI | Meyer, Haynes, et al., 1965 | RDSH |
De-protonation reactions
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 371.0 ± 2.5 | kcal/mol | G+TS | Mishima, Kinoshita, et al., 2002 | gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 363.3 ± 2.0 | kcal/mol | IMRE | Mishima, Kinoshita, et al., 2002 | gas phase; Reprotonation likely to be on C-1, giving 1-alkyl-cycloheptatriene - JEB; B |
References
Go To: Top, Reaction thermochemistry data, 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.
Mishima, Kinoshita, et al., 2002
Mishima, M.; Kinoshita, T.; Hattori, Y.; Takeuchi, K.,
Gas-phase acidities of cycloheptatrienes: effects of alkyl groups on the stability of carbanions,
Eur. J. Mass Spectrom., 2002, 8, 1, 359-366, https://doi.org/10.1255/ejms.499
. [all data]
Egger, 1968
Egger, K.W.,
The thermal intramolecular rearrangement of methyl-1,3,5-cycloheptatrienes in the gas phase. II. thermodynamic data from equilibrium studies of the positional isomers,
J. Am. Chem. Soc., 1968, 90, 1-5. [all data]
Meyer, Haynes, et al., 1965
Meyer, F.; Haynes, P.; McLean, S.; Harrison, A.G.,
An electron impact study of some C8H10 isomers,
Can. J. Chem., 1965, 43, 211. [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]
Notes
Go To: Top, Reaction thermochemistry data, 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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