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Green Synthesis of Quinoline-Based Ionic Liquid

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6,8-Dibromo-quinoline.

Ismail Celik, Mehmet Akkurt, Osman Cakmak

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study examines the molecular structure of C(9)H(5)Br(2)N, revealing a nearly planar configuration. Crystal analysis shows significant pi-pi stacking and bromine-bromine interactions, influencing molecular arrangement.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure Analysis

Background:

Understanding the solid-state behavior of organic molecules is crucial for materials science.
Dibrominated pyridine derivatives offer unique electronic and structural properties.
Intermolecular interactions dictate crystal packing and material properties.

Purpose of the Study:

To elucidate the detailed molecular geometry and crystal packing of C(9)H(5)Br(2)N.
To investigate the nature and significance of intermolecular forces in the crystal lattice.
To provide insights into structure-property relationships for this class of compounds.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.

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Analysis of atomic deviations from planarity and dihedral angles.

Identification and quantification of intermolecular interactions, including pi-pi stacking and halogen bonding.

Main Results:

The C(9)H(5)Br(2)N molecule exhibits a near-planar conformation with a root-mean-square deviation of 0.027 Å.
A small dihedral angle of 1.5(3)° between the pyridine and benzene rings was observed.
Significant pi-pi stacking interactions between adjacent molecules were identified (centroid-centroid distance = 3.634(4) Å).
Short bromine-bromine contacts (3.4443(13) Å) were detected, suggesting potential halogen bonding.

Conclusions:

The crystal structure of C(9)H(5)Br(2)N is characterized by significant intermolecular pi-pi stacking and Br-Br interactions.
These interactions play a key role in organizing the molecules within the crystal lattice.
The findings contribute to the understanding of halogenated aromatic systems and their solid-state assembly.