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Updated: Jan 11, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Oxidation-induced σ-aromaticity in halogenated cycloalkanes.
Slavko Radenković1, Slađana Đorđević1
1University of Kragujevac, Faculty of Science, P. O. Box 60, 34000 Kragujevac, Serbia. slavkoradenkovic@kg.ac.rs.
Neutral halogenated cycloalkanes can become σ-aromatic dicationic species via oxidation. These novel compounds exhibit significant σ-electron delocalization in halogen rings, resembling known aromatic systems.
Area of Science:
- * Computational chemistry
- * Organic chemistry
- * Quantum chemistry
Background:
- * Investigating novel aromatic systems is crucial for understanding chemical bonding.
- * Cyclic halogenated compounds offer unique structural and electronic properties.
- * Exploring σ-aromaticity in non-traditional ring systems expands the definition of aromaticity.
Purpose of the Study:
- * To investigate the potential for σ-aromaticity in dicationic halogenated cycloalkanes.
- * To explore the conversion of neutral cycloalkanes into σ-aromatic dicationic species.
- * To compare the electronic properties of these systems with known aromatic compounds.
Main Methods:
- * Magnetically Induced Current Density (MICD) calculations.
- * Electron Density of Delocalized Bonds (EDDB) analysis.
- * Aromatic Stabilization Energy (ASE) calculations.
Main Results:
- * Significant σ-electron delocalization was observed in the halogen atom rings of the studied dications.
- * All applied aromaticity indices consistently supported the presence of σ-aromaticity.
- * The electronic delocalization closely mirrors that of the C6I62+ system.
Conclusions:
- * Nonaromatic, neutral halogenated cycloalkanes can be oxidized to form σ-aromatic dicationic species.
- * The observed σ-aromaticity does not always adhere to Hückel's rule, suggesting complex electronic interactions.
- * Results can be explained by selection rules governing molecular orbital transitions.
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