Quinuclidine

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
CAS Number	100-76-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:38420 ;
ChEMBL	ChEMBL1209648 ;
ChemSpider	7246 ;
ECHA InfoCard	100.002.625
PubChem CID	7527;
UNII	XFX99FC5VI ;
CompTox Dashboard (EPA)	DTXSID2057607 ;
	InChI InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N ; InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Key: SBYHFKPVCBCYGV-UHFFFAOYAA;
	SMILES N12CCC(CC1)CC2;
Properties
Chemical formula	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).
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	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 pK_a 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. It is classified as a soft base and its donor properties are discussed in the ECW model.

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

Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich
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).
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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[1] Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich

[iupac2013-2] 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.