2-Cyclohexen-1-one
- Formula: C6H8O
- Molecular weight: 96.1271
- IUPAC Standard InChI: InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2
- IUPAC Standard InChIKey: FWFSEYBSWVRWGL-UHFFFAOYSA-N
- CAS Registry Number: 930-68-7
- 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: Cyclohex-2-en-1-one; Cyclohexen-2-one; 1-Cyclohexen-3-one; 2-Cyclohexenone; 2-Cyclohexene-1-one; 2-Cyclohexenone-1; Cyclohexen-3-one; cyclohex-2-enone
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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
View reactions leading to C6H8O+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.23 ± 0.05 | PE | Holmes, Terlouw, et al., 1979 | LLK |
| 9.20 | PE | Schweig, Vermeer, et al., 1974 | Vertical value; LLK |
| 9.37 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
De-protonation reactions
+
=
By formula: C6H7O- + H+ = C6H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1496. ± 8.8 | kJ/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1464. ± 8.4 | kJ/mol | IMRE | Bartmess and Kiplinger, 1986 | 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.
Holmes, Terlouw, et al., 1979
Holmes, J.L.; Terlouw, J.K.; Vijfhuizen, P.C.; A'Campo, C.,
Metastable ion studies XII-Molecular and fragment ion structures for isomeric C4H6O2 acids,
Org. Mass Spectrom., 1979, 14, 204. [all data]
Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U.,
A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy,
Chem. Phys. Lett., 1974, 26, 229. [all data]
Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen,
J. Mol. Struct., 1974, 21, 231. [all data]
Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P.,
'Kinetic' vs. thermodynamic acidities of enones in the gas phase,
J. Org. Chem., 1986, 51, 2173. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
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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