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Updated: Oct 1, 2025
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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Synthesis and structures of three benzoannelated macrobicyclic diamides
Gary L N Smith1, Richard W Taylor2
1Department of Chemistry, San Diego Miramar College, San Diego, CA 92126, USA.
Acta Crystallographica. Section C, Structural Chemistry
|March 4, 2022
Summary
This study reports the synthesis and structures of three novel macrocyclic compounds. These compounds feature unique ring systems and donor atom arrangements, influencing their structural properties.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Crystal Engineering
Background:
- Macrocyclic compounds are crucial in host-guest chemistry and molecular recognition.
- Designing novel macrocycles with specific cavity sizes and donor atom arrangements is essential for targeted applications.
- Previous research has explored various macrocyclic architectures, but further structural diversity is needed.
Purpose of the Study:
- To synthesize and characterize three new macrocyclic compounds with dibenzo-fused tetraoxadiazacyclooctadecine cores.
- To investigate the structural features and solid-state properties of these novel compounds.
- To compare the structural differences arising from variations in ring size and donor atom composition.
Main Methods:
- Multi-step organic synthesis to construct the macrocyclic frameworks.
- Single-crystal X-ray diffraction to determine the solid-state structures.
- Spectroscopic techniques (NMR, IR) for structural confirmation.
Main Results:
- Successful synthesis of three macrocyclic compounds (I, II, and III) with distinct structural characteristics.
- Compounds I and II possess two 15-membered rings and one 18-membered ring, while compound III features three 18-membered rings.
- Solid-state structures reveal minimal amide group movement in I and II, contrasting with a larger cavity and altered donor atom orientation in III.
Conclusions:
- The synthesized macrocycles represent novel additions to the field of supramolecular chemistry.
- Structural variations significantly impact the cavity size and donor atom positioning within the macrocyclic framework.
- These findings provide a basis for the rational design of macrocycles for specific molecular recognition and host-guest applications.
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