Bicyclo[2.2.1]hept-2-en-5-one
- Formula: C7H8O
- Molecular weight: 108.1378
- IUPAC Standard InChI: InChI=1S/C7H8O/c8-7-4-5-1-2-6(7)3-5/h1-2,5-6H,3-4H2
- IUPAC Standard InChIKey: HUQXEIFQYCVOPD-UHFFFAOYSA-N
- CAS Registry Number: 694-98-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Bicyclo(2.2.1)hept-5-en-2-one; Dehydronorcamphor; Norcamphor, dehydro-; 2-Norbornen-5-one; 2-Norbornenone; 5-Norbornen-2-one; (±)-Bicyclo[2.2.1]hept-5-ene-2-one
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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C7H8O+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 845.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 813.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.86 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
| 8.90 ± 0.02 | PE | Chadwick, Frost, et al., 1971 | Vertical value; LLK |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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| 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 | P. VAINIOTALO, DEPT. CHEM., UNIV. JOENSUU, JOENSUU, FINLAND |
| NIST MS number | 138871 |
Gas Chromatography
Go To: Top, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-5 | 931. | Plettner, Mohle, et al., 2005 | 30. m/0.25 mm/0.25 μm; Program: 50C(5min) => 5C/min => 100C(4min) => 50C/min => 250C(20min) |
References
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L.,
Photoelectron spectra of norbornanones and norbornenones,
J. Am. Chem. Soc., 1971, 93, 4962. [all data]
Plettner, Mohle, et al., 2005
Plettner, E.; Mohle, A.; Mwangi, M.T.; Griscti, J.; Patrick, B.O.; Nair, R.; Batchelor, R.J.; Einstein, F.,
2-Chlorobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2-chlorobicyclo[2.2.1]heptane-2-carboxamide as precursors of bicyclo[2.2.1]hept-5-en-2-one and bicyclo[2.2.1]heptan-2-one: resolution, absolute configuration and hydrogen-bonding properties,
Tetrahedron: Asymmetry, 2005, 16, 16, 2754-2763, https://doi.org/10.1016/j.tetasy.2005.07.016
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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