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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)

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

Published on: November 22, 2016

p-Phenyl-enedimethanaminium dibromide.

Yuan Zhang¹, Meng Ting Han

¹Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a salt, revealing cations and anions connected by hydrogen bonds. These interactions form layered structures within the crystal lattice, similar to its chloride counterpart.

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Area of Science:

Crystallography
Solid-state chemistry
Supramolecular chemistry

Background:

Understanding the structural properties of organic salts is crucial for materials science.
Investigating hydrogen bonding interactions provides insights into crystal packing and network formation.
Comparison with analogous compounds aids in identifying structure-property relationships.

Purpose of the Study:

To elucidate the crystal structure of the title salt, C(8)H(14)N(2)·2Br(-).
To analyze the intermolecular interactions, specifically hydrogen bonds, within the crystal lattice.
To compare the structural features with its chloride analogue.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
Analysis of crystallographic data revealed the symmetry elements and atomic positions.
Intermolecular interactions were identified and characterized through bond analysis.

Main Results:

The crystal structure of C(8)H(14)N(2)·2Br(-) was successfully determined.
The cation, C(8)H(14)N(2) (2+), exhibits a crystallographically imposed centre of symmetry.
N-H⋯Br hydrogen bonds link cations and anions, forming distinct layers parallel to the bc plane.
The compound was found to be isostructural with the corresponding chloride salt.

Conclusions:

The crystal structure confirms the presence of a centrosymmetric cation and highlights the role of N-H⋯Br hydrogen bonds.
The layered structure formed by hydrogen bonding is a key feature of this salt.
Isostructurality with the chloride analogue suggests similar packing motifs and intermolecular forces.