Quinuclidine

Quinuclidine^[1]

Names

IUPAC name

1-Azabicyclo[2.2.2]octane

Identifiers

100-76-5^Y

CHEBI:38420^Y

7246^Y

InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2^Y
Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N^Y
InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
Key: SBYHFKPVCBCYGV-UHFFFAOYAA

Jmol-3D images

N12CCC(CC1)CC2

Properties

C₇H₁₃N

111.18 g/mol

0.97g/cm3

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 (pK_a)

12.1 (conjugate acid)

Hazards

Flash point

36.5 °C (97.7 °F; 309.6 K)

Except where noted otherwise, data is 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 pKa of the conjugate acid of 11.0.^[2] This is due to greater availability of the nitrogen lone pair . It can be prepared by reduction of quinuclidone.

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

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

References

↑ Quinuclidine at Sigma-Aldrich
↑ 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.