2,5-Norbornadiene
- Formula: C7H8
- Molecular weight: 92.1384
- IUPAC Standard InChIKey: SJYNFBVQFBRSIB-UHFFFAOYSA-N
- 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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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
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:
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 |
---|---|---|---|---|---|
ΔfH°gas | 57. ± 6. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
25.239 | 298.15 | Walsh R., 1975 | Selected value of S(298.15 K) is in excellent agreement with that calculated by force field method [ Lenz T.G., 1989].; GT |
25.421 | 300. | ||
34.529 | 400. | ||
42.151 | 500. | ||
48.279 | 600. | ||
53.250 | 700. | ||
57.349 | 800. | ||
60.791 | 900. | ||
63.690 | 1000. |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess
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: C7H8 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22. ± 6. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.5 ± 1.8 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 391.3 ± 1.5 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
ΔrG° | 389.0 ± 5.0 | kcal/mol | IMRB | Wright and Beauchamp, 1981 | gas phase; B |
By formula: C7H8 + 2H2 = C7H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -70.8 ± 0.3 | kcal/mol | Chyd | Doering, Roth, et al., 1988 | gas phase; ALS |
ΔrH° | -69.77 ± 0.36 | kcal/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; ALS |
ΔrH° | -68.11 ± 0.41 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid; ALS |
By formula: C7H8 = C5H6 + C2H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 28.00 ± 0.50 | kcal/mol | Kin | Walsh and Wells, 1975 | gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 28.36 ± 0.32 kcal/mol; ALS |
By formula: C7H8 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 14. ± 1. | kcal/mol | Ciso | Harel, Adamson, et al., 1987 | liquid phase; solvent: Cyclohexane; Photocalorimetry; ALS |
By formula: C5H6 + C2H2 = C7H8
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.0 ± 0.5 | kcal/mol | Eqk | Walsh and Wells, 1975 | gas phase; ALS |
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
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.38 ± 0.04 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 203.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 196.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.4 | PE | Ohno, Ishide, et al., 1985 | LBLHLM |
8.35 | PI | Traeger and McLoughlin, 1978 | LLK |
8.35 | PE | Traeger and McLoughlin, 1978 | LLK |
8.42 | PE | Demeo and Yencha, 1970 | RDSH |
8.42 ± 0.02 | PI | Demeo and El-Sayed, 1970 | RDSH |
8.69 | PE | Houk, Rondan, et al., 1983 | Vertical value; LBLHLM |
8.7 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
8.73 | PE | Worley and Webb, 1980 | Vertical value; LLK |
8.73 | PE | Worley, Webb, et al., 1979 | Vertical value; LLK |
8.69 | PE | Kobayashi, 1978 | Vertical value; LLK |
8.69 | PE | Cowling, Johnstone, et al., 1973 | Vertical value; LLK |
8.6 | PE | Palmer and Findlay, 1972 | Vertical value; LLK |
8.69 | PE | Heilbronner and Martin, 1972 | Vertical value; LLK |
8.70 | PE | Bischof, Heilbronner, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 9.25 | H | PI | Traeger and McLoughlin, 1978 | LLK |
C7H7+ | 9.75 | H | EI | Dolejsek, Hanus, et al., 1962 | RDSH |
C7H7+ | 9.6 | H | EI | Meyerson, McCollum, et al., 1961 | RDSH |
De-protonation reactions
C7H7- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 399.5 ± 1.8 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 391.3 ± 1.5 | kcal/mol | IMRB | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
ΔrG° | 389.0 ± 5.0 | kcal/mol | IMRB | Wright and Beauchamp, 1981 | gas phase; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 4000-1250 CM-1, 10% IN CS2 FOR 1250-450 CM-1) VS. SOLVENT; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-4679 |
NIST MS number | 229218 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
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]
Walsh and Wells, 1975
Walsh, R.; Wells, J.M.,
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]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Harel, Adamson, et al., 1987
Harel, Y.; Adamson, A.W.; Kutal, C.; Grutsch, P.A.; Yasufuku, K.,
Photocalorimetry. 6. Enthalpies of isomerization of norbornadiene and of substituted norbornadienes to corresponding quadricyclenes,
J. Phys. Chem., 1987, 91, 901-904. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions 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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