Anion-Exchange Properties of Trifluoroacetate and Triflate Salts of N-Alkylammonium Resorcinarenes

作者：Pan Fangfang; Beyeh Ngong Kodiah^*; Bertella Stefania; Rissanen Kari^*

来源：Chemistry-An Asian Journal, 2016, 11(5): 782-788.

DOI：10.1002/asia.201501335

• anion binding
• crystal engineering
• host-guest systems
• macrocycles
• weak interactions

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.

• 出版日期2016-3-4