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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...

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Updated: Jun 1, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Published on: November 22, 2016

4-Carb-oxy-pyridinium bromide.

Yingchun Wang¹

¹Ordered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study details the crystal structure of a pyridinium bromide compound, highlighting the specific torsion angles of its hydroxy and carbonyl groups. Molecular interactions, including hydrogen bonds, form stable chains within the crystal lattice.

Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Understanding the three-dimensional arrangement of atoms in crystalline solids is crucial for predicting material properties.
Hydrogen bonding plays a significant role in molecular self-assembly and the stability of crystal structures.
Pyridinium compounds are versatile building blocks in various chemical applications.

Purpose of the Study:

To elucidate the crystal structure of a specific pyridinium bromide compound.
To analyze the conformational preferences of functional groups within the pyridinium ring.
To identify and characterize the intermolecular interactions stabilizing the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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Analysis of torsion angles provided insights into the conformation of the hydroxy and carbonyl groups.

Hydrogen bond analysis identified key intermolecular interactions (N-H⋯Br, O-H⋯Br, C-H⋯O).

Main Results:

The crystal structure of C(6)H(6)NO(2)⁺·Br⁻ was successfully determined.
Torsion angles of 164.8(4)° (hydroxy) and -17.6(6)° (carbonyl) relative to the pyridinium ring were quantified.
Intermolecular hydrogen bonds (N-H⋯Br, O-H⋯Br, C-H⋯O) were observed, forming chains along the b-axis.

Conclusions:

The crystal structure reveals specific conformational preferences for the hydroxy and carbonyl groups in this pyridinium bromide.
Intermolecular hydrogen bonding is a key factor in the observed crystal packing and stability.
The findings contribute to the understanding of structure-property relationships in pyridinium-based materials.