Pyridinium chloride

Last updated
Pyridinium chloride [1] [2]
Pyridiniumchlorid.svg
The chemical structure of pyridinium chloride
Pyridinium-chloride-3D-balls.png
Names
IUPAC name
Pyridinium chloride
Other names
Pyridine hydrochloride
Identifiers
3D model (JSmol)
ECHA InfoCard 100.010.026 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-027-4
PubChem CID
UNII
  • InChI=AOJFQRQNPXYVLM-UHFFFAOYSA-N
  • C1=CC=[NH+]C=C1.[Cl-]
Properties
C5H6NCl
Molar mass 115.56 g/mol
AppearanceHygroscopic white crystals
Density 1.34 g/cm3
Melting point 144 °C (291 °F; 417 K)
Boiling point Decomposes
85 g / 100 mL
Solubility Soluble in chloroform, ethanol, insoluble in diethyl ether
Vapor pressure 1 (0 °C)
Acidity (pKa)5
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
0
0
Flash point Non-flammable
Non-flammable
Lethal dose or concentration (LD, LC):
1600 mg/kg (oral, rat)
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

Contents

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]

Related Research Articles

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Acyl halide Chemical compound

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Pyridinium chlorochromate Chemical compound

Pyridinium chlorochromate (PCC) is a yellow-orange salt with the formula [C5H5NH]+[CrO3Cl]. It is a reagent in organic synthesis used primarily for oxidation of alcohols to form carbonyls. A variety of related compounds are known with similar reactivity. PCC offers the advantage of the selective oxidation of alcohols to aldehydes or ketones, whereas many other reagents are less selective.

Acetyl chloride Chemical compound

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Oxalyl chloride Chemical compound

Oxalyl chloride is a chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

Benzoyl chloride Chemical compound

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

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Organolead compound

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Pyridine-<i>N</i>-oxide Chemical compound

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Sulfonamide Class of chemical compounds

In chemistry, the sulfonamide functional group (also spelled sulphonamide) is -S(=O)2-NH2, a sulfonyl group connected to an amine group. Relatively speaking this group is unreactive. The amine center is no longer basic. The S-N bond is cleaved only with difficulty. Because of the rigidity of the functional group, sulfonamides are typically crystalline. For this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.

References

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