Halogen bonds on substituted dibromonitrobenzene derivatives

Area of Science:

• Organic Chemistry
• Crystallography
• Computational Chemistry

Background:

• Halogen bonding is a crucial noncovalent interaction with broad applications in photonics, pharmaceuticals, and supramolecular chemistry.
• Understanding these interactions is vital for designing novel materials and understanding biological processes.

Purpose of the Study:

• To synthesize and characterize five dibromonitrobenzene derivatives.
• To investigate the molecular structure, supramolecular arrangement, and halogen bonding interactions within these compounds.
• To elucidate the role of halogen bonding in the solid-state stabilization of these derivatives.

Main Methods:

• Synthesis of five dibromonitrobenzene derivatives.
• Solid-state characterization using X-ray diffraction and Hirshfeld surface analysis.
• Theoretical calculations including frontier molecular orbital, molecular electrostatic potential, and quantum theory of atoms in molecules (QTAIM) at the M06-2X/6-311+G(d,p) level.

Main Results:

• Detailed molecular structures and supramolecular arrangements were determined for the synthesized compounds.
• Hirshfeld surface analysis confirmed the presence and significance of halogen bonding interactions.
• Theoretical calculations provided insights into the electronic properties and bonding characteristics, supporting the observed interactions.

Conclusions:

• The synthesized dibromonitrobenzene derivatives exhibit significant halogen bonding interactions.
• These halogen bonding interactions play a critical role in the stabilization of the crystalline solid-state structures.
• The findings contribute to the fundamental understanding of halogen bonding and its applications in materials science and drug discovery.