The atypical solubility of silver(i) pentafluorobenzoate and its use as a catch-and-release agent

Silver(I) pentafluorobenzoate (1) possesses an atypical solubility for a silver(I) carboxylate, demonstrating solubility in a range of etheric and aromatic solvents. This versatile solubility has been probed crystallographically by single crystal X-ray diffraction (SCXRD) due to the myriad of solid-state structures that were isolated from a variety of solvents, providing insights into how 1 can be utilised as a reuseable crystallisation aid. This potential as a reuseable ‘catch-and-release’ agent to obtain the solid-state structures of liquid natural products was screened with the racemic dihydrocarvone, achiral eucalyptol, and the chiral R-carvone, and found to be viable. The results of these screenings demonstrated improved crystallographic outcomes than other prior attempts utilising different methodologies (e.g., encapsulation).