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Discrimination of Chiral BCPs by Möbius Cyclacene: A DFT Study
Azhar Abbas1, Muhammad Huzaifa1, Muhammad Nabeel Ghayur2
1H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
The Journal of Physical Chemistry. A
|June 5, 2026
Summary
A novel twisted cyclacene host framework enables direct enantiomeric recognition of chiral bicyclo[1.1.1]pentane (BCP) analogues. R enantiomers showed stronger binding and selectivity, highlighting potential for enantioselective separation in pharmaceuticals.
Area of Science:
- Supramolecular Chemistry
- Computational Chemistry
- Materials Science
Background:
- Chiral discrimination is crucial for developing enantiomerically pure pharmaceuticals, as stereochemistry impacts efficacy and safety.
- Conventional chiral resolution methods often rely on diastereomer formation.
- Direct enantiomeric recognition offers a more efficient approach for chiral separation.
Purpose of the Study:
- To investigate the enantiomeric recognition capabilities of a nitrogen-substituted twisted cyclacene host for chiral bicyclo[1.1.1]pentane (BCP) analogues.
- To explore the host-guest interactions using computational simulations.
- To provide theoretical insights for designing advanced host systems for chiral separation.
Main Methods:
- Density Functional Theory (DFT) simulations were employed to study the interactions between the cyclacene host and BCP derivatives.
- Analysis of key interaction parameters including binding energies, hydrogen bonding, noncovalent interaction (NCI), and electron density difference (EDD) maps.
- Systematic exploration of four R/S enantiomeric pairs of BCP derivatives.
Main Results:
- The cyclacene host demonstrated direct enantiomeric discrimination of BCP analogues.
- R enantiomers exhibited stronger binding affinities and enhanced chiral selectivity compared to S enantiomers.
- Specific BCP derivatives (BCP3 and BCP4) showed the highest degrees of chiral discrimination.
Conclusions:
- The nitrogen-substituted twisted cyclacene is a promising host for enantioselective separation of BCP analogues.
- The findings offer valuable theoretical guidance for designing nanostructured host systems for chiral recognition.
- This research supports the advancement of supramolecular materials for pharmaceutical purification and asymmetric sensing.
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