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
- 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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Reaction thermochemistry data
Go To: Top, 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
B - John E. Bartmess
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Individual Reactions
=
By formula: C7H8 = C7H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -90. ± 30. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
C7H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1672. ± 7.5 | kJ/mol | G+TS | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1637. ± 6.3 | kJ/mol | IMRB | Lee and Squires, 1986 | gas phase; Between EtNH2, nPrNH2; B |
| ΔrG° | 1628. ± 21. | kJ/mol | IMRB | Wright and Beauchamp, 1981 | gas phase; B |
+ 2
=
By formula: C7H8 + 2H2 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -296. ± 1. | kJ/mol | Chyd | Doering, Roth, et al., 1988 | gas phase; ALS |
| ΔrH° | -291.9 ± 1.5 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; ALS |
| ΔrH° | -285.0 ± 1.7 | kJ/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° | 117.2 ± 2.1 | kJ/mol | Kin | Walsh and Wells, 1975 | gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 118.7 ± 1.3 kJ/mol; ALS |
=
By formula: C7H8 = C7H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 59. ± 4. | kJ/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° | -117. ± 2. | kJ/mol | Eqk | Walsh and Wells, 1975 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
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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