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Biasing hydrogen bond donating host systems towards chemical warfare agent recognition

Hiscock, Jennifer R., Wells, Neil J., Ede, Jayne A., Gale, Philip A., Sambrook, Mark R. (2016) Biasing hydrogen bond donating host systems towards chemical warfare agent recognition. Organic and Biomolecular Chemistry, 14 (40). pp. 9560-9567. ISSN 1477-0520. (doi:10.1039/c6ob01210h) (KAR id:60102)

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Abstract

A series of neutral ditopic and negatively charged, monotopic host molecules have been evaluated for their ability to bind chloride and dihydrogen phosphate anions, and neutral organophosphorus species dimethyl methylphosphonate (DMMP), pinacolyl methylphosphonate (PMP) and the chemical warfare agent (CWA) pinacolyl methylphosphonofluoridate (GD, soman) in organic solvent via hydrogen bonding. Urea, thiourea and boronic acid groups are shown to bind anions and neutral guests through the formation of hydrogen bonds, with the urea and thiourea groups typically exhibiting higher affinity interactions. The introduction of a negative charge on the host structure is shown to decrease anion affinity, whilst still allowing for high stability host-GD complex formation. Importantly, the affinity of the host for the neutral CWA GD is greater than for anionic guests, thus demonstrating the potential for selectivity reversal based on charge repulsion.

Item Type: Article
DOI/Identification number: 10.1039/c6ob01210h
Divisions: Faculties > Sciences > School of Physical Sciences
Depositing User: Matthias Werner
Date Deposited: 26 Jan 2017 11:43 UTC
Last Modified: 23 Jan 2020 04:12 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/60102 (The current URI for this page, for reference purposes)
Hiscock, Jennifer R.: https://orcid.org/0000-0002-1406-8802
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