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 Copy

  
• IUPAC Standard InChIKey: SBYHFKPVCBCYGV-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Condensed phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 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

Ionization energy determinations

Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.

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]

Westrum, Wong, et al., 1970
Westrum, E.F., Jr.; Wong, W-K.; Morawetz, E., Thermodynamics of globular molecules. XVIII. Heat capacities and transitional behavior of 1-azabicyclo[2.2.2]octane and 3-oxabicyclo[3.2.2]nonane. Sublimation behavior of five globular molecules, J. Phys. Chem., 1970, 74, 2542-2547. [all data]

Westrum and Wong, 1970
Westrum, E.F.; Wong, W.-K., Thermodynamics of globular molecules. XVIII. Heat capacities and transitional behavior of 1-azabicyclo[2.2.2]octane and 3-oxabicyclo[3.2.2] nonane..................., J. Phys. Chem., 1970, 74, 2542. [all data]

Brown and Sujishi, 1948
Brown, Herbert C.; Sujishi, Sei, Dissociation of the Addition Compound of Trimethylboron with Quinuclidine; Further Evidence for the Steric Configuration of Triethylamine ¹, J. Am. Chem. Soc., 1948, 70, 9, 2878-2881, https://doi.org/10.1021/ja01189a013 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH°	Enthalpy of sublimation 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.
• Customer support for NIST Standard Reference Data products.