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Updated: Jun 1, 2026
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Hydro-nium perchlorate-dibenzo-18-crown-6 (1/1): monoclinic polymorph
Summary
This study details the crystal structure of a dibenzo-18-crown-6 complex with hydronium and perchlorate ions. It reveals intricate hydrogen bonding and molecular interactions within the crystal lattice.
Area of Science:
- Supramolecular Chemistry
- Crystallography
- Organic Chemistry
Background:
- Crown ethers are macrocyclic compounds known for their ability to complex cations.
- Dibenzo-18-crown-6 is a widely studied crown ether with a rigid structure.
- Understanding host-guest interactions is crucial in supramolecular chemistry.
Purpose of the Study:
- To elucidate the crystal structure of the complex formed between dibenzo-18-crown-6, hydronium ions, and perchlorate anions.
- To investigate the hydrogen bonding network and intermolecular interactions within the crystal.
- To characterize the conformation and packing of the dibenzo-18-crown-6 molecules.
Main Methods:
- Single-crystal X-ray diffraction analysis was performed to determine the three-dimensional structure.
- Hydrogen bonding interactions were identified and analyzed based on bond lengths and angles.
- Crystal packing was examined to understand the arrangement of molecules in the solid state.
Main Results:
- The asymmetric unit contains two molecules/ions of each component: dibenzo-18-crown-6, hydronium (H3O+), and perchlorate (ClO4-).
- Hydronium ions are complexed within the cavities of the dibenzo-18-crown-6 molecules, forming O-H⋯O and O-H⋯(O,O) links.
- Perchlorate anions participate in O-H⋯O hydrogen bonds with the hydronium ions.
- Dibenzo-18-crown-6 molecules adopt a butterfly conformation with approximate C2v symmetry.
- Intermolecular interactions, including C-H⋯O and C-H⋯π bonds, stabilize the crystal packing.
Conclusions:
- The study provides a detailed structural characterization of a novel supramolecular assembly.
- The observed hydrogen bonding network highlights the specific interactions between the crown ether, hydronium, and perchlorate ions.
- The crystal packing is governed by a combination of hydrogen bonding and van der Waals forces, including C-H⋯O and C-H⋯π interactions.
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