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
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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Other data available:
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	21. ± 7.	kcal/mol	AVG	N/A	Average of 8 values; Individual data points

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
26.94	298.15	Walsh R., 1975	Two sets of calculated functions are given by [ Walsh R., 1976] for two vibrational assignments. The difference between the two sets is about 8 J/mol*K for S(T) values. S(298.15 K) recommended here is in good agreement with value obtained from detail force field calculation [ Lenz T.G., 1989].; GT
27.15	300.
37.55	400.
46.34	500.
53.47	600.
59.30	700.
64.10	800.
68.16	900.
71.58	1000.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	7.09 ± 0.40	kcal/mol	Ccb	Hall, Smith, et al., 1973	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1007.0 ± 0.4	kcal/mol	Ccb	Hall, Smith, et al., 1973	Corresponding Δ_fHº_liquid = 7.11 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	10.62 ± 0.48	kcal/mol	Ccr	Steele, Chirico, et al., 1996	Hfusion=3.2±0.2 kJ/mol; ALS
Δ_fH°_solid	12.8 ± 0.76	kcal/mol	Ccb	Steele, 1978	ALS
Δ_fH°_solid	9.89 ± 0.33	kcal/mol	Ccb	Kozina, Bychikhina, et al., 1976	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-1010.55 ± 0.47	kcal/mol	Ccr	Steele, Chirico, et al., 1996	Hfusion=3.2±0.2 kJ/mol; Corresponding Δ_fHº_solid = 10.62 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1012.7 ± 0.76	kcal/mol	Ccb	Steele, 1978	Corresponding Δ_fHº_solid = 12.8 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-1009.83 ± 0.32	kcal/mol	Ccb	Kozina, Bychikhina, et al., 1976	Corresponding Δ_fHº_solid = 9.90 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
31.05	298.15	Steele, 1978	DH
31.05	297.	Hall, Smith, et al., 1973	DH

Gas phase ion energetics data

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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

+ = 2-Norbornene

By formula: C₇H₉^- + H⁺ = C₇H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	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
Δ_rG°	393.9 ± 3.0	kcal/mol	IMRB	Lee and Squires, 1986	gas phase; Between NH₃, EtNH₂. Assigned as vinylic site by authors.; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Walsh R., 1975
Walsh R., The enthalpy of formation of bicyclo[2.2.1]hepta-2,5-diene. Thermodynamic functions of bicyclo[2.2.1]heptane and bicyclo[2.2.1]hepta-2,5-diene, J. Chem. Thermodyn., 1975, 7, 149-154. [all data]

Walsh R., 1976
Walsh R., The enthalpy of formation and thermodynamic functions of bicyclo[2.2.1]hept-2-ene, J. Chem. Thermodyn., 1976, 8, 55-60. [all data]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Hall, Smith, et al., 1973
Hall, H.K., Jr.; Smith, C.D.; Baldt, J.H., Enthalpies of formation of norticyclene, norbornene, norbornadiene, and quadricyclane, J. Am. Chem. Soc., 1973, 95, 3197-3201. [all data]

Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol, J. Chem. Eng. Data, 1996, 41, 1285-1302. [all data]

Steele, 1978
Steele, W.V., The standard enthalpies of formation of a series of C₇, bridged-ring hydrocarbons: norbornane, norbornene, nortricyclene, norbornadiene, and quadricyclane, J. Chem. Thermodyn., 1978, 10, 919-927. [all data]

Kozina, Bychikhina, et al., 1976
Kozina, M.P.; Bychikhina, L.V.; Gal'chenko, G.L.; Mil'vitskaya, E.M.; Ordubadi, M.; Plate, A.F., Enthalpies of nortricyclene and norbornene formation, Dokl. Akad. Nauk SSSR, 1976, 226, 1105-1108. [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]

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

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,solid	Constant pressure heat capacity of solid
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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