Pyridinium_chloride

Pyridinium chloride

Pyridinium chloride

Chemical compound

Pyridinium chloride is an organic chemical compound with a formula of C5H5NHCl.

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Preparation

Pyridinium chloride can be produced by passing hydrogen chloride in pyridine dissolved in diethyl ether. The chemical formula is as follows:

Acidity

Containing a pyridinium ion, pyridinium chloride has a pKa of approximately 5, slightly more acidic than that of typical amines. This is due to the hybridization of the nitrogen: the nitrogen is sp2 hybridized and more electronegative than those nitrogens in ammonium cations, which are sp3 hybridized. Hence they are stronger acids than amines and can be more easily deprotonated by bases.[3]

References

  1. [1]
    "Pyridine hydrochloride(628-13-7) MSDS Melting Point Boiling Point Density Storage Transport". ChemicalBook. Retrieved 2019-03-22.
  2. [2]
    Wilson, Michael W. (2001). "Pyridinium Chloride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289x.rp287m. ISBN 9780470842898.
  3. [3]
    "Pyridine: synthesis and reactivity | BrainyResort". Brainy Resort. 2016-11-08. Retrieved 2019-03-28.
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