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

Autor:	Howard T. Dodd, Alexander S. Cragg, Adam H. Lansley, Flavia Fucassi, Mark R. Sambrook, Jayne A. Ede, Hannah Cave, Peter J. Cragg
Rok vydání:	2019
Předmět:	inorganic chemicals Chemical Warfare Agents animal structures 010405 organic chemistry Hydrogen bond Thio General Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences carbohydrates (lipids) enzymes and coenzymes (carbohydrates) chemistry.chemical_compound Thiourea chemistry Polymer chemistry Urea Derivative (chemistry)
Zdroj:	Supramolecular Chemistry. 31:703-712
ISSN:	1029-0478 1061-0278
DOI:	10.1080/10610278.2019.1659268
Popis:	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.
Databáze:	OpenAIRE
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