Biasing hydrogen bond donating host systems towards chemical warfare agent recognition
Biasing hydrogen bond donating host systems towards chemical warfare agent recognition
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.
1-8
Hiscock, Jennifer R.
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Wells, Neil J.
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Ede, Jayne A.
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Gale, Philip A.
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Sambrook, Mark R.
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Hiscock, Jennifer R.
2e1470fc-e298-492e-b50a-f1b590d224db
Wells, Neil J.
72cad8bf-b0db-4152-beb9-d6e6171f989b
Ede, Jayne A.
eff6cc53-5040-450f-ba22-a98db29766ef
Gale, Philip A.
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Sambrook, Mark R.
fc7e74a4-e746-48c2-a836-b1b09b204f42
Hiscock, Jennifer R., Wells, Neil J., Ede, Jayne A., Gale, Philip A. and Sambrook, Mark R.
(2016)
Biasing hydrogen bond donating host systems towards chemical warfare agent recognition.
Organic & Biomolecular Chemistry, .
(doi:10.1039/C6OB01210H).
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.
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Accepted/In Press date: 18 August 2016
e-pub ahead of print date: 20 September 2016
Organisations:
Organic Chemistry: SCF
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Local EPrints ID: 400665
URI: http://eprints.soton.ac.uk/id/eprint/400665
ISSN: 1477-0520
PURE UUID: f754f66b-1032-4bb9-945e-cce2a4a2ba86
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Date deposited: 21 Sep 2016 15:51
Last modified: 15 Mar 2024 05:54
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Contributors
Author:
Jennifer R. Hiscock
Author:
Neil J. Wells
Author:
Jayne A. Ede
Author:
Philip A. Gale
Author:
Mark R. Sambrook
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