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 Copy

  
• IUPAC Standard InChIKey: WTQBISBWKRKLIJ-UHFFFAOYSA-N Copy
• 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
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• 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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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

De-protonation reactions

C₈H₉^- +  =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Weiss and Hammond, 1978
Weiss, R.G.; Hammond, G.S., J. Am. Chem. Soc., 1978, 100, 1172. [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

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• 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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