2-Norbornene

• Formula: C₇H₁₀
• Molecular weight: 94.1543
• IUPAC Standard InChI: InChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 Copy

  
• IUPAC Standard InChIKey: JFNLZVQOOSMTJK-UHFFFAOYSA-N Copy
• CAS Registry Number: 498-66-8
• 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: Bicyclo[2.2.1]hept-2-ene; Bicyclo[2.2.1]heptene; Norbornene; Norbornylene; Norcamphene; Norfenchene; 2-Norbornylene; 3,6-Endomethylenecyclohexene; Bicyclo[2.2.1]-2-heptene; NSC 120425; 8,9,10-trinorborn-2-ene
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
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Reaction thermochemistry 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  =

By formula: C₇H₉^- + H⁺ = C₇H₁₀

 +  =

By formula: H₂ + C₇H₁₀ = C₇H₁₂

 +  =

By formula: C₇H₁₀ + C₂HF₃O₂ = C₉H₁₁F₃O₂

 +  =

By formula: C₇H₁₀ + HCl = C₇H₁₁Cl

=  + 

By formula: C₇H₁₀ = C₅H₆ + C₂H₄

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

 +  =

By formula: C₇H₉^- + H⁺ = C₇H₁₀

References

Go To: Top, Reaction thermochemistry data, 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.

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]

Doering, Roth, et al., 1988
Doering, W.E.; Roth, W.R.; Breuckmann, R.; Figge, L.; Lennartz, H.-W.; Fessner, W.-D.; Prinzbach, F.H., Verbotene Reaktionen. - [2 + 2]-Cycloreversion starrer Cyclobutane, Chem. Ber., 1988, 121, 1-9. [all data]

Rogers, Choi, et al., 1980
Rogers, D.W.; Choi, L.S.; Girellini, R.S., Heats of hydrogenation and formation of quadricyclene, norbornadiene, norbornene, and nortricyclene, J. Phys. Chem., 1980, 84, 1810-1814. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Walsh and Wells, 1976
Walsh, R.; Wells, J.M., The enthalpy of formation and thermodynamic functions of bicyclo[2,2,1]hept-2-ene, J. Chem. Thermodyn., 1976, 8, 55-60. [all data]

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]

Wen, Hitchcock, et al., 1990
Wen, A.T.; Hitchcock, A.P.; Werstiuk, N.H.; Nguyen, N.; Leigh, W.J., Studies of electronic excited states of substituted norbornenes by UV absorption, electron energy loss, and HeI photoelectron spectroscopy, Can. J. Chem., 1990, 68, 1967. [all data]

Holmes and McGillivray, 1971
Holmes, J.L.; McGillivray, D., The mass spectra of isomeric hydrocarbons-I: Norbornene and nortricyclene; The mechanisms and energetics of their fragmentations, Org. Mass Spectrom., 1971, 5, 1349. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method, J. Am. Chem. Soc., 1970, 92, 19. [all data]

Muller and Herberhold, 1968
Muller, J.; Herberhold, M., Massenspektroskopische Untersuchungen an C₅H₅Mn(CO)₃ und C₅H₅Mn(CO)₂ L-Komplexen, J. Organometal. Chem., 1968, 13, 399. [all data]

Steele, Jennings, et al., 1965
Steele, W.C.; Jennings, B.H.; Botyos, G.L.; Dudek, G.O., An electron impact study of norbornenyl and nortricyclyl chlorides, J. Org. Chem., 1965, 30, 2886. [all data]

Winstein and Lossing, 1964
Winstein, S.; Lossing, F.P., On the question of homoconjugation in 1,4,7-cyclononatriene, J. Am. Chem. Soc., 1964, 86, 4485. [all data]

Houk, Rondan, et al., 1983
Houk, K.N.; Rondan, N.G.; Paddon-Row, M.N.; Jefford, C.W.; Huy, P.T.; Burrow, P.D.; Jordan, K.D., Ionization potentials, electron affinities, and molecular orbitals of 2-substituted norbornadienes. Theory of 1,2 and homo-1,4 carbene cycloaddition selectivities, J. Am. Chem. Soc., 1983, 105, 5563. [all data]

Barraclough, Bilgic, et al., 1979
Barraclough, P.; Bilgic, S.; Pedley, J.B.; Rogers, A.J.; Young, D.W., Conjugative and homoconjugative effects in 2-heterobicyclo[3.2.1]octa-3,6-dienes, Tetrahedron, 1979, 35, 99. [all data]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [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]

Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M., Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds, Tetrahedron, 1974, 30, 2477. [all data]

Heilbronner and Martin, 1972
Heilbronner, E.; Martin, H.D., The π-orbital sequence in norbornadiene and related hydrocarbons, Helv. Chim. Acta, 1972, 55, 1490. [all data]

Bischof, Heilbronner, et al., 1971
Bischof, P.; Heilbronner, E.; Prinzbach, H.; Martin, H.D., A photoelectron-spectroscopic investigation of the homoconjugative interaction between π- and Walsh-orbitals in endo- and exo- cyclopropano-norbornene, Helv. Chim. Acta, 1971, 54, 1072. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  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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