title: Trapping of organophosphorus chemical nerve agents in water with amino acid functionalized baskets.
abstract: We prepared eleven amino-acid functionalized baskets and used (1) H NMR spectroscopy to quantify their affinity for entrapping dimethyl methylphosphonate (DMMP, 118 Å(3) ) in aqueous phosphate buffer at pH=7.0±0.1; note that DMMP guest is akin in size to chemical nerve agent sarin (132 Å(3) ). The binding interaction (Ka ) was found to vary with the size of substituent groups at the basket's rim. In particular, the degree of branching at the first carbon of each substituent had the greatest effect on the host-guest interaction, as described with the Verloop's B1 steric parameter. The branching at the remote carbons, however, did not perturb the encapsulation, which is important for guiding the design of more effective hosts and catalysts in future.
authors.affiliation: Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus OH 43210 (USA), Fax: (+1) 614-292-1685.
authors.forename: Yian
authors.initials: Y
authors.lastname: Ruan
authors.forename: Erdin
authors.initials: E
authors.lastname: Dalkiliç
authors.forename: Paul W
authors.initials: PW
authors.lastname: Peterson
authors.forename: Aroh
authors.initials: A
authors.lastname: Pandit
authors.forename: Arif
authors.initials: A
authors.lastname: Dastan
authors.forename: Jason D
authors.initials: JD
authors.lastname: Brown
authors.forename: Shane M
authors.initials: SM
authors.lastname: Polen
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Hadad
authors.forename: Jovica D
authors.initials: JD
authors.lastname: Badjić
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002619:Chemical Warfare Agents / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D007700:Kinetics; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002619:Chemical Warfare Agents; D009943:Organophosphorus Compounds; D014867:Water; C031116:dimethyl methylphosphonate
keywords: host-guest systems; linear free-energy relationship; molecular encapsulation; molecular recognition; nerve agents