2,5-Norbornadiene

• Formula: C₇H₈
• Molecular weight: 92.1384
• IUPAC Standard InChI: InChI=1S/C7H8/c1-2-7-4-3-6(1)5-7/h1-4,6-7H,5H2 Copy

  
• IUPAC Standard InChIKey: SJYNFBVQFBRSIB-UHFFFAOYSA-N Copy
• CAS Registry Number: 121-46-0
• 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]hepta-2,5-diene; Bicyclo[2.2.1]heptadiene; Norbornadiene; 3,6-Methano-1,4-cyclohexadiene; Dicycloheptadiene; Bicyclo[2.2.1]-2,5-heptadiene; NSC 13672; 8,9,10-trinorborna-2,5-diene
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 C₇H₈⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇^- +  =

By formula: C₇H₇^- + H⁺ = C₇H₈

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

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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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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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]

Ohno, Ishide, et al., 1985
Ohno, K.; Ishide, T.; Naitoh, Y.; Izumi, Y., Study of stereochemical properties of molecular orbitals by penning ionization electron spectroscopy, J. Am. Chem. Soc., 1985, 107, 8082. [all data]

Traeger and McLoughlin, 1978
Traeger, J.C.; McLoughlin, R.G., A photoionization study of the energetics of C₇H₇⁺ ion formed from C₇H₈ precursors, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 319. [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]

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]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Worley and Webb, 1980
Worley, S.D.; Webb, T.R., The electronic structure of transition-metal carbonyl complexes of norbornadiene and mesitylene, J. Organomet. Chem., 1980, 192, 139. [all data]

Worley, Webb, et al., 1979
Worley, S.D.; Webb, T.R.; Gibson, D.H.; Ong, T.-S., On the electronic structures of cyclobutadiene trimethylenemethane, J. Organomet. Chem., 1979, 168, 16. [all data]

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

Palmer and Findlay, 1972
Palmer, M.H.; Findlay, R.H., Ab initio molecular orbital calculations, the electronic structure and electron spectrum of norbornadiene, Chem. Phys. Lett., 1972, 15, 416. [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]

Dolejsek, Hanus, et al., 1962
Dolejsek, Z.; Hanus, V.; Prinzbach, H., Das massenspektrometrische Verhalten von Quadricyclen, Angew. Chem., 1962, 74, 902. [all data]

Meyerson, McCollum, et al., 1961
Meyerson, S.; McCollum, J.D.; Rylander, P.N., Organic ions in the gas phase. VIII. Bicycloheptadiene, J. Am. Chem. Soc., 1961, 83, 1401. [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]

Wright and Beauchamp, 1981
Wright, C.A.; Beauchamp, J.L., Infrared spectra of gas phase ions and their use in elucidating reaction mechanisms. Identification of C₇H₇- structural isomers by multiphoton electron detachment using a low-powered laser, J. Am. Chem. Soc., 1981, 103, 6499. [all data]

Diez, Guillen, et al., 1990
Diez, M.A.; Guillen, M.D.; Blanco, C.G.; Bermejo, J., Chromatographic study of methylcyclopentadiene dimers and iso-dimers and determination of their boiling points, J. Chromatogr., 1990, 508, 363-374, https://doi.org/10.1016/S0021-9673(00)91279-2 . [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]

Stopp, Engewald, et al., 1978
Stopp, I.; Engewald, W.; Kühn, H.; Welsch, Th., Molekülstruktur und retentionsverhalten. VIII. Zum gaschromatographischen retentionsverhalten von dicyclopentadienderivaten, J. Chromatogr., 1978, 147, 21-30, https://doi.org/10.1016/S0021-9673(00)85113-4 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J., Composition of the oil from waste tires. 1. Fraction boiling at yp to 160 0C, Proc. Estonian Acad. Sci. Chem., 1999, 48, 1, 30-39. [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization 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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