[Substituted cyclodextrins as chelating reagents for ethers, thioethers and yperite]

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Analytical Chemistry

Context:

• Mustard gas (HD) is a chemical warfare agent requiring effective neutralization strategies.
• Cyclodextrins are cyclic oligosaccharides known for their ability to form inclusion complexes with various molecules.
• Understanding the interaction between HD and cyclodextrins is crucial for developing detoxification methods.

Purpose:

• To investigate the complexation of mustard gas (HD) and its derivatives (ethers, thioethers) with cyclodextrins using Nuclear Magnetic Resonance (NMR) spectroscopy.
• To determine the stoichiometry and affinity constants of these inclusion complexes.
• To assess the potential of cyclodextrins for HD chelation.

Summary:

• NMR studies revealed a 1:1 stoichiometry for the complexation of mustard gas (HD) and related thioethers/ethers with both natural alpha-cyclodextrin (ACD) and substituted beta-cyclodextrins.
• Affinity constants for these complexes were found to be relatively weak, ranging from 5 M(-1) to 100 M(-1).
• Despite weak affinities, the findings indicate that cyclodextrin-based chelation of HD is feasible, particularly with chemically modified cyclodextrins designed for enhanced binding.

Impact:

• This research provides foundational data for the design of cyclodextrin-based systems for mustard gas detection and detoxification.
• Highlights the potential of supramolecular chemistry in addressing chemical security threats.
• Suggests avenues for further research into optimizing cyclodextrin structures for improved HD binding affinity.