title: Anion-Exchange Properties of Trifluoroacetate and Triflate Salts of N-Alkylammonium Resorcinarenes.
abstract: The synthesis of N-benzyl- and N-cyclohexylammonium resorcinarene trifluoroacetate (TFA) and triflate (OTf) salt receptors was investigated. Solid-state analysis by single-crystal X-ray diffraction revealed that the N-alkylammonium resorcinarene salts (NARSs) with different upper substituents had different cavity sizes and different affinities for anions. Anion-exchange experiments by mixing equimolar amounts of N-benzylammonium resorcinarene trifluoroacetate and N-cyclohexylammonium resorcinarene triflate, as well as N-benzylammonium resorcinarene triflate and N-cyclohexylammonium resorcinarene trifluoroacetate showed that the NARS with flexible benzyl groups preferred the larger OTf anion, whereas the rigid cyclohexyl groups preferred the smaller TFA anions. The anion-exchange processes were confirmed in the solid state by single-crystal and powder X-ray diffraction experiments and in the gas phase by electrospray ionization mass spectrometry.
authors.affiliation: University of Jyvaskyla, Finland, Department of Chemistry, Nanoscience Center, P.O. Box 35, FI-40014, Jyvaskyla, Finland.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Pan
authors.affiliation: University of Jyvaskyla, Finland, Department of Chemistry, Nanoscience Center, P.O. Box 35, FI-40014, Jyvaskyla, Finland. kodiah.beyeh@aalto.fi.|Aalto University School of Science, Department of Applied Physics, P.O. Box 15100, FI-00076, Aalto, Espoo, Finland. kodiah.beyeh@aalto.fi.
authors.forename: Ngong Kodiah
authors.identifier: http://orcid.org/0000-0003-3935-1812
authors.initials: NK
authors.lastname: Beyeh
authors.affiliation: University of Jyvaskyla, Finland, Department of Chemistry, Nanoscience Center, P.O. Box 35, FI-40014, Jyvaskyla, Finland.|Università Degli Studi Di Parma, Dipartimento Di Chimica, Parco Area delle Scienze 17 A, 43124, Parma, Italy.
authors.forename: Stefania
authors.initials: S
authors.lastname: Bertella
authors.affiliation: University of Jyvaskyla, Finland, Department of Chemistry, Nanoscience Center, P.O. Box 35, FI-40014, Jyvaskyla, Finland. kari.t.rissanen@jyu.fi.
authors.forename: Kari
authors.identifier: http://orcid.org/0000-0002-7282-8419
authors.initials: K
authors.lastname: Rissanen
mesh_terms: D000838:Anions / Q000737:chemistry*; D050339:Benzylammonium Compounds / Q000737:chemistry; D047250:Calixarenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004146:Dioxanes / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D012492:Salts / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000838:Anions; D050339:Benzylammonium Compounds; D004146:Dioxanes; D008698:Mesylates; D012492:Salts; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine; D014269:Trifluoroacetic Acid; C025223:1,4-dioxane
keywords: anion binding; crystal engineering; host-guest systems; macrocycles; weak interactions