Extraction of alkali metal picrates by crown ethers having uncharged coordinating flexible side-chains

Crown ethers were synthesized which have a flexible, neutral side-chain capable of providing the crown ether-bound metal with an additional binding site from the axial direction. Liquid—liquid extraction of alkali metal picrates with these crown ethers was studied; the extraction is compared with that of the normal crown ethers as well as those crown ethers with a proton-dissociable side-chain. The neutral side-chain may assist or suppress the ease of metal extraction depending on the site of the ligating atom on the chain. An anionic ligating side-chain interacts favorably with the lighter metals, resulting in a net decrease in the metal extraction selectivity.