title: Rational design, synthesis, and application of a new receptor for the molecular recognition of tricarboxylate salts in aqueous media.
abstract: A rational design of a tripodal receptor for the molecular recognition of tricarboxylate salts in aqueous media, based on squaramide, has been performed using high-level DFT calculations (RI-BP86/SVP level of theory) in solution using the COSMO treatment, including some preliminary ab initio calculations at the higher RI-MP2/TZVP level of theory, comparing the ability of squaramide to bind carboxylate salts with two widely used guanidinium salts. The tripodal receptor has been synthesized using a new methodology that has been recently reported by some of us, and its capability of recognizing several mono-, di-, and tricarboxylate salts has been studied experimentally by means of microcalorimetry experiments in a very high competitive media, H(2)O:EtOH 1:3. These experiments give enthalpic and entropic data, which are unfortunately scarce in the literature of molecular recognition of anions. Finally, a fluorimetric ensemble of the receptor with fluorescein has been found to be useful for the fluorimetric determination of zinc citrate in a commercial toothpaste using competition assays.
authors.affiliation: Department of Chemistry, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, 07122 Palma de Mallorca, Spain. toni.frontera@uib.es
authors.forename: Antonio
authors.initials: A
authors.lastname: Frontera
authors.forename: Jeroni
authors.initials: J
authors.lastname: Morey
authors.forename: Antonia
authors.initials: A
authors.lastname: Oliver
authors.forename: M Neus
authors.initials: MN
authors.lastname: Piña
authors.forename: David
authors.initials: D
authors.lastname: Quiñonero
authors.forename: Antoni
authors.initials: A
authors.lastname: Costa
authors.forename: Pablo
authors.initials: P
authors.lastname: Ballester
authors.forename: Pere M
authors.initials: PM
authors.lastname: Deyà
authors.forename: Eric V
authors.initials: EV
authors.lastname: Anslyn
mesh_terms: D001665:Binding Sites; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions; D014233:Tricarboxylic Acids / Q000302:isolation & purification*
chemical_list: D003503:Cyclobutanes; D000644:Quaternary Ammonium Compounds; D012996:Solutions; D014233:Tricarboxylic Acids