Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 703-712 |
| Number of pages | 10 |
| Journal | Supramolecular Chemistry |
| Volume | 31 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 1 Sep 2019 |
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Keywords
- Chemical warfare agents
- colorimetric sensors
- hydrogen bonding
- macrocycles
- simulants
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Hydrogen-bonding interactions in crown-(thio)urea complexes with anions, chemical warfare agents and simulants. / Cave, Hannah; Ede, Jayne A.; Sambrook, Mark; Dodd, Howard; Fucassi, Flavia; Cragg, Alexander; Lansley, Adam; Cragg, Peter.
In: Supramolecular Chemistry, Vol. 31, No. 11, 01.09.2019, p. 703-712.Research output: Contribution to journal › Article
TY - JOUR
T1 - Hydrogen-bonding interactions in crown-(thio)urea complexes with anions, chemical warfare agents and simulants
AU - Cave, Hannah
AU - Ede, Jayne A.
AU - Sambrook, Mark
AU - Dodd, Howard
AU - Fucassi, Flavia
AU - Cragg, Alexander
AU - Lansley, Adam
AU - Cragg, Peter
PY - 2019/9/1
Y1 - 2019/9/1
N2 - 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.
AB - 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.
KW - Chemical warfare agents
KW - colorimetric sensors
KW - hydrogen bonding
KW - macrocycles
KW - simulants
UR - http://www.scopus.com/inward/record.url?scp=85071487793&partnerID=8YFLogxK
U2 - 10.1080/10610278.2019.1659268
DO - 10.1080/10610278.2019.1659268
M3 - Article
VL - 31
SP - 703
EP - 712
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
SN - 1061-0278
IS - 11
ER -