2,3-Diazabicyclo[2.2.1]-hept-2-ene
- Formula: C5H8N2
- Molecular weight: 96.1304
- IUPAC Standard InChI: InChI=1S/C5H8N2/c1-2-5-3-4(1)6-7-5/h4-5H,1-3H2
- IUPAC Standard InChIKey: IJDUBDHNOXAHCQ-UHFFFAOYSA-N
- CAS Registry Number: 2721-32-6
- Chemical structure:
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 46.8 | kcal/mol | Ccb | Engel, Wood, et al., 1974 | see Engel, Melaugh, et al., 1976 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 36.35 | kcal/mol | Ccb | Engel, Wood, et al., 1974 | see Engel, Melaugh, et al., 1976 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -779.86 ± 0.17 | kcal/mol | Ccb | Engel, Wood, et al., 1974 | see Engel, Melaugh, et al., 1976 |
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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 13.2 ± 0.1 | kcal/mol | N/A | Engel, Melaugh, et al., 1976 | AC |
| ΔsubH° | 10.49 | kcal/mol | V | Engel, Wood, et al., 1974 | see Engel, Melaugh, et al., 1976; ALS |
| ΔsubH° | 10.5 | kcal/mol | N/A | Engel, Wood, et al., 1974 | DRB |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
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By formula: C5H8N2 = C5H8 + N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.2 ± 2.5 | kcal/mol | Cpha | Herman and Goodman, 1989 | solid phase; solvent: Acetonitrile/water |
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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.45 ± 0.04 | PE | Boyd, Bunzli, et al., 1973 | LLK |
| 8.94 | PE | Houk, Chang, et al., 1975 | Vertical value; LLK |
| 8.82 | PE | Schmidt, Schweig, et al., 1974 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Engel, Wood, et al., 1974
Engel, P.S.; Wood, J.L.; Sweet, J.A.; Margrave, J.L.,
Thermochemistry of azoalkanes,
J. Am. Chem. Soc., 1974, 96, 2381-2387. [all data]
Engel, Melaugh, et al., 1976
Engel, P.S.; Melaugh, R.A.; Mansson, M.; Timberlake, J.W.; Garner, A.W.; Rossini, F.D.,
Thermochemistry of nine diazenes (azo compounds),
J. Chem. Thermodyn., 1976, 8, 607-621. [all data]
Herman and Goodman, 1989
Herman, M.S.; Goodman, J.L.,
Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry,
J. Am. Chem. Soc., 1989, 111, 1849-1854. [all data]
Boyd, Bunzli, et al., 1973
Boyd, R.J.; Bunzli, J.C.; Snyder, J.P.; Heyman, M.L.,
Photoelectron spectra of 2,3-diazabicyclo[2.2 n]alk-2-enes (n = 1,2,3,4),
J. Am. Chem. Soc., 1973, 95, 6478. [all data]
Houk, Chang, et al., 1975
Houk, K.N.; Chang, Y.-M.; Engel, P.S.,
Photoelectron spectroscopy of azo compounds,
J. Am. Chem. Soc., 1975, 97, 1824. [all data]
Schmidt, Schweig, et al., 1974
Schmidt, H.; Schweig, A.; Trost, B.M.; Neubold, H.B.; Scudder, P.H.,
Influence of geometry on cyclopropyl participation in the thermolysis of azo compounds. A photoelectron spectroscopic rationalization,
J. Am. Chem. Soc., 1974, 96, 622. [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, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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