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
View 3d structure (requires JavaScript / HTML 5) - 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
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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 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 |
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.
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]
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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