Quinuclidine
- Formula: C7H13N
- Molecular weight: 111.1848
- IUPAC Standard InChI: InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
- IUPAC Standard InChIKey: SBYHFKPVCBCYGV-UHFFFAOYSA-N
- CAS Registry Number: 100-76-5
- 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: 1-Azabicyclo[2.2.2]octane; 1,4-Ethylenepiperidine; 4-Azabicyclo[2.2.2]octane
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Gas phase thermochemistry data
Go To: Top, 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 | -4.3 ± 1.3 | kJ/mol | Ccr | Wong and Westrum, 1971 | see Westrum and Wong, 1967 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, References, Notes
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
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 983.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 952.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.5 | PE | Aue and Bowers, 1979 | LLK |
| 7.5 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
| 7.50 ± 0.09 | PE | Aue, Webb, et al., 1975 | LLK |
| 8.0 | PE | Aue and Bowers, 1979 | Vertical value; LLK |
| 8.06 ± 0.015 | PE | Bieri and Heilbronner, 1974 | Vertical value; LLK |
| 8.02 | PE | Bischof, Hashmall, et al., 1969 | Vertical value; RDSH |
References
Go To: Top, Gas phase 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.
Wong and Westrum, 1971
Wong, S.S.; Westrum, E.F., Jr.,
Enthalpies of formation of globular molecules. II. Three bicyclooctanes and two bicyclononanes,
J. Am. Chem. Soc., 1971, 93, 5317-5321. [all data]
Westrum and Wong, 1967
Westrum, E.F., Jr.; Wong, S.,
Strain energies and thermal properties of globular and polynuclear aromatic molecules,
AEC Rept. Coo-1149-92, Contract AT(11-1)-1149, 1967, 1-7. [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]
Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [all data]
Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Photoelectron spectrum and gas-phase basicity of manxine. Evidence for a planar bridgehead nitrogen,
J. Am. Chem. Soc., 1975, 97, 4136. [all data]
Bieri and Heilbronner, 1974
Bieri, G.; Heilbronner, E.,
Der einfluss von substituenten in stellung 4 auf das n-ionisations- zpotenial des chinuclidins,
Helv. Chim. Acta, 1974, 57, 546. [all data]
Bischof, Hashmall, et al., 1969
Bischof, P.; Hashmall, J.A.; Heilbronner, E.; Hornung, V.,
Nitrogen lone pair interaction in 1,4-diaza-bicyclo[2.2.2]octane (DABCO),
Tetrahedron Lett., 1969, 4025. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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