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
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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
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. |
Condensed phase 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 51.10 ± 0.72 | kcal/mol | Ccb | Steele, 1978 | ALS |
ΔfH°liquid | 42.72 ± 0.24 | kcal/mol | Ccb | Hall, Smith, et al., 1973 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -982.72 ± 0.72 | kcal/mol | Ccb | Steele, 1978 | Corresponding ΔfHºliquid = 51.10 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -974.35 ± 0.24 | kcal/mol | Ccb | Hall, Smith, et al., 1973 | Corresponding ΔfHºliquid = 42.73 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -979.6 | kcal/mol | Ccb | Skuratov, Kozina, et al., 1958 | Corresponding ΔfHºliquid = 48.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.53 | 298.15 | Steele, 1978 | DH |
27.75 | 297. | Hall, Smith, et al., 1973 | DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 362.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 363.4 | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 355.4 | K | N/A | Turner, Meador, et al., 1957 | Uncertainty assigned by TRC = 0.8 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 254.0 | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 205.15 | K | N/A | Brooks and Pilcher, 1959 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.1 ± 0.4 | kcal/mol | AVG | N/A | Average of 9 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.03 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 300. to 364. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
0.457 | 255.6 | Bykova, Smirnova, et al., 2004 | AC |
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, 2 | 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
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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, Condensed phase thermochemistry data, Phase change 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
View image of digitized spectrum (can be printed in landscape orientation).
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, Condensed phase thermochemistry data, Phase change 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]
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]
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]
Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D.,
Heats of combustion of cyclic compounds,
Bull. Chem. Thermodyn., 1958, 1, 21. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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. [all data]
Brooks and Pilcher, 1959
Brooks, J.H.; Pilcher, G.,
A Simple Melting Point Calorimeter for Moderately Precise Determination of Purity,
J. Chem. Soc., 1959, 1959, 1535. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Bykova, Smirnova, et al., 2004
Bykova, T.A.; Smirnova, N.N.; Nikishchenkova, L.V.; Belov, G.P.; Novikova, E.V.,
Zh. Fiz. Khim., 2004, 78, 11, 1944. [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, 2
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, Condensed phase thermochemistry data, Phase change 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 Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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