N-Alkyl pyrrolidone ether podands as versatile alkali metal ion chelants

Abstract

This work explores the coordination chemistry of a bis(pyrrolidone) ether ligand. Pyrrolidones are commercially important functional groups because of the high polarity and hence high hydrophilicity and surface affinity. An array of alkali metal ion complexes of a podand bearing two pendant pyrrolidone functionalities, namely 1-{2-[2-(2-oxo-pyrrolid-1-yl)-ethoxy]-ethyl}-pyrrolid-2- one (1) are reported. Reaction of this ligand with sodium hexafluorophosphate gives two discrete species of formulae [Na(1)2]PF6 (3) and [Na3(H2O)2(μ-1)2](PF 6)3 (4), and a coordination polymer {[Na 3(μ3-1)3(μ2-1)](PF 6)3}n (5). The same reaction in methanol gives a 1:1 complex, namely [Na2(μ-1)2(MeOH) 2](PF6)2 (6). Use of tetraphenyl borate as a less coordinating counter ion gives [Na2(1)2(H 2O)4](BPh4)2 (7) and [Na 2(1)4](BPh4)2 (8). Two potassium complexes have also been isolated, a monomer [K(1)2]PF6 (9) and a cyclic tetramer [K4(μ4-H2O) 2(μ-1)4](PF6)4 (10). The structures illustrate the highly polar nature of the amide carbonyl moiety within bis(pyrrolidone) ethers with longer interactions to the ether oxygen atom. The zinc complex is also reported and {[ZnCl2(μ-1)]} n (11) exhibits bonding only to the carbonyl moieties. The ether oxygen atom is not necessary for Na+ complexation as exemplified by the structure of the sodium complex of the analogue 1,3-bis(pyrrolid-2-on-1-yl) butane (2). Reaction of compound 1 with lithium salts results in isolation of the protonated ligand. © 2014 The Royal Society of Chemistry.