2-Norbornene
- Formula: C7H10
- Molecular weight: 94.1543
- IUPAC Standard InChIKey: JFNLZVQOOSMTJK-UHFFFAOYSA-N
- 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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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 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 199.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 192.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.6 | PE | Wen, Hitchcock, et al., 1990 | LL |
8.80 ± 0.01 | EI | Holmes and McGillivray, 1971 | LLK |
8.82 | PE | Demeo and Yencha, 1970 | RDSH |
8.81 ± 0.02 | PI | Demeo and El-Sayed, 1970 | RDSH |
8.83 | PE | Bodor, Dewar, et al., 1970 | RDSH |
9.0 ± 0.1 | EI | Muller and Herberhold, 1968 | RDSH |
8.95 ± 0.15 | EI | Steele, Jennings, et al., 1965 | RDSH |
9.05 | EI | Winstein and Lossing, 1964 | RDSH |
9.2 | PE | Wen, Hitchcock, et al., 1990 | Vertical value; LL |
≤8.97 | PE | Houk, Rondan, et al., 1983 | Vertical value; LBLHLM |
8.95 | PE | Barraclough, Bilgic, et al., 1979 | Vertical value; LLK |
8.97 | PE | Kobayashi, 1978 | Vertical value; LLK |
8.97 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
8.97 | PE | Asmus and Klessinger, 1974 | Vertical value; LLK |
8.97 | PE | Heilbronner and Martin, 1972 | Vertical value; LLK |
8.95 | PE | Bischof, Heilbronner, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H6+ | 9.22 ± 0.01 | C2H4 | EI | Holmes and McGillivray, 1971 | LLK |
C5H6+ | 9.58 ± 0.15 | ? | EI | Steele, Jennings, et al., 1965 | RDSH |
C6H5+ | 13.8 ± 0.3 | ? | EI | Steele, Jennings, et al., 1965 | RDSH |
C6H7+ | 10.46 ± 0.01 | CH3 | EI | Holmes and McGillivray, 1971 | LLK |
C6H7+ | 11.2 ± 0.15 | CH3 | EI | Steele, Jennings, et al., 1965 | RDSH |
C7H7+ | 13.6 ± 0.3 | H2+H | EI | Steele, Jennings, et al., 1965 | RDSH |
C7H9+ | 11.0 ± 0.01 | H | EI | Holmes and McGillivray, 1971 | LLK |
C7H9+ | 11.5 ± 0.15 | H | EI | Steele, Jennings, et al., 1965 | RDSH |
De-protonation reactions
By formula: C7H9- + H+ = C7H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 402.1 ± 3.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 393.9 ± 3.0 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; 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 | OV-101 | 100. | 731. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 726. | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | Squalane | 100. | 721.2 | Diez, Guillen, et al., 1990 | N2; Column length: 45. m; Column diameter: 0.5 mm |
Capillary | Squalane | 80. | 714.6 | Diez, Guillen, et al., 1990 | N2; Column length: 45. m; Column diameter: 0.5 mm |
Capillary | SE-54 | 100. | 741.1 | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | SE-54 | 80. | 735.2 | Diez, Guillen, et al., 1990 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | OV-101 | 100. | 731. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | OV-101 | 80. | 726. | Bermejo, Blanco, et al., 1987 | N2; Column length: 25. m; Column diameter: 0.23 mm |
Capillary | Squalane | 40. | 706.7 | Stopp, Engewald, et al., 1978 | Column length: 70. m; Column diameter: 0.23 mm |
Packed | Squalane | 27. | 704. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 710. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 715. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 720. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | PONA | 699. | Zhang, Ding, et al., 2009 | 50. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min |
Capillary | OV-101 | 727. | Orav, Kailas, et al., 1999 | 50. m/0.20 mm/0.50 μm, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 716. | Chen, 2008 | Program: not specified |
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.
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]
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]
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]
Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T.,
Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline,
Chromatographia, 2009, 70, 3/4, 511-518, https://doi.org/10.1365/s10337-009-1174-0
. [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, Gas Chromatography, 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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