Quinuclidine

From Wikipedia, the free encyclopedia
Quinuclidine[1]
Skeletal formula of quinuclidine
Ball-and-stick model of quinuclidine
Names
Preferred IUPAC name
1-Azabicyclo[2.2.2]octane[2]
Other names
Quinuclidine[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.625 Edit this at Wikidata
UNII
  • InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 checkY
    Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N checkY
  • InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
    Key: SBYHFKPVCBCYGV-UHFFFAOYAA
  • N12CCC(CC1)CC2
Properties
C7H13N
Molar mass 111.188 g·mol−1
Density 0.97 g/cm3
Melting point 157 to 160 °C (315 to 320 °F; 430 to 433 K)
Boiling point 149.5 °C (301.1 °F; 422.6 K) at 760 mmHg
Acidity (pKa) 11.0 (conjugate acid)
Hazards
Flash point 36.5 °C (97.7 °F; 309.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
Infobox references

Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 11.0.[3] It can be prepared by reduction of quinuclidone.

In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids.

The compound is structurally related to DABCO, in which the other bridgehead is also nitrogen, and to tropane, which has a slightly different carbon frame.

Quinuclidine is found as a structural component of some biomolecules including quinine.

References[]

  1. ^ Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich
  2. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name quinuclidine is retained for general nomenclature only (see Table 2.6).
  3. ^ Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. (1998). "Azatriquinanes: Synthesis, Structure, and Reactivity". J. Org. Chem. 63 (17): 6016–6020. doi:10.1021/jo980788s. PMID 11672206.
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