Bicyclo[2.2.1]hept-2-ene, 5-methylene-
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChI: InChI=1S/C8H10/c1-6-4-7-2-3-8(6)5-7/h2-3,7-8H,1,4-5H2
- IUPAC Standard InChIKey: WTQBISBWKRKLIJ-UHFFFAOYSA-N
- CAS Registry Number: 694-91-7
- 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: 5-Methylene-2-norbornene; 2-Methylene-5-norbornene; 2-Norbornene, 5-methylene-; 5-Methylene-2-norbornylene; 5-Methylenebicyclo(2.2.1)hept-2-ene; 5-Methylenenorbornene; 5-Methylenebicyclo[2.2.1]-2-heptene
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Gas phase ion energetics data
Go To: Top, 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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C8H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.01 | PE | Asmus and Klessinger, 1974 | Vertical value; LLK |
| 8.93 | PE | Cowling, Johnstone, et al., 1973 | Vertical value; LLK |
De-protonation reactions
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1632. ± 8.8 | kJ/mol | G+TS | Lee and Squires, 1986 | gas phase; Ca. 1 kcal < H2O; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1603. ± 8.4 | kJ/mol | IMRB | Lee and Squires, 1986 | gas phase; Ca. 1 kcal < H2O; B |
Gas Chromatography
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | BP-1 | 100. | 800. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
| Capillary | BP-1 | 80. | 800. | Bermejo, Blanco, et al., 1987 | N2; Column length: 12. m; Column diameter: 0.22 mm |
| Capillary | OV-101 | 100. | 803. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
| Capillary | OV-101 | 80. | 798. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 803. | El-Massry, El-Ghorab, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 3. K/min, 220. C @ 40. min; Tstart: 35. C |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M.,
Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds,
Tetrahedron, 1974, 30, 2477. [all data]
Cowling, Johnstone, et al., 1973
Cowling, S.A.; Johnstone, R.A.W.; Gorman, A.A.; Smith, P.G.,
Photoelectron spectrum of 5-methylenenorborn-2-ene and through-space interactions (homobutadiene conjugation),
J. Chem. Soc., Chem. Commun., 1973, 627. [all data]
Lee and Squires, 1986
Lee, R.E.; Squires, R.R.,
Anionic homoaromaticity: A gas phase experimental study,
J. Am. Chem. Soc., 1986, 105, 5078. [all data]
Bermejo, Blanco, et al., 1987
Bermejo, J.; Blanco, C.G.; Diez, M.A.; Guillén, M.D.,
Kováts retention indices of selected mono and polycyclic olefins,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1987, 10, 8, 461-463, https://doi.org/10.1002/jhrc.1240100809
. [all data]
El-Massry, El-Ghorab, et al., 2009
El-Massry, K.F.; El-Ghorab, A.H.; Shaaban, H.A.; Shibamoto, T.,
Chemical compositions and antioxidant/antimicrobial activities of various samples prepared from Schinus terebinthifolius leaves cultivated in Egipt,
J. Agric. Food Chem., 2009, 57, 12, 5265-5270, https://doi.org/10.1021/jf900638c
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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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