Hydrogen-bonding interactions in crown-(thio)urea complexes with anions, chemical warfare agents and simulants

Hannah Cave, Jayne A. Ede, Mark Sambrook, Howard Dodd, Flavia Fucassi, Alexander Cragg, Adam Lansley, Peter Cragg

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Benzocrown ethers incorporating phenyl and nitrophenyl urea and thiourea moieties were synthesised. Both the nitrophenyl urea and thiourea derivative gave a fluoride-specific colorimetric response but only the urea derivative bound the organophosphonate nerve agent simulants dimethyl methylphosphonate (DMMP) and diisopropyl methylphosphonate (DIMP). This suggested an application as sensors for the nerve agents sarin, soman and cyclosarin which release fluoride upon hydrolysis. Although no fluoride-induced response was observed in the UV-visible spectrum, binding to soman was determined by 1H NMR. DFT computational simulations suggested that the two crowns adopt different conformations in which both can bind fluoride but only the urea derivative can bind DMMP, DIMP and soman. The results show that, for this system, simulant- and soman-binding behaviours are in good agreement.
    Original languageEnglish
    Pages (from-to)703-712
    Number of pages10
    JournalSupramolecular Chemistry
    Volume31
    Issue number11
    DOIs
    Publication statusPublished - 1 Sept 2019

    Keywords

    • Chemical warfare agents
    • colorimetric sensors
    • hydrogen bonding
    • macrocycles
    • simulants

    Fingerprint

    Dive into the research topics of 'Hydrogen-bonding interactions in crown-(thio)urea complexes with anions, chemical warfare agents and simulants'. Together they form a unique fingerprint.

    Cite this