An iodide/anion exchange route to benzimidazolylidene silver complexes from benzimidazolium iodide: Crystal structures of N,N′-dibutylbenzimidazolylidene silver chloride, bromide, cyanide and nitrate

Syntheses of N,N′-dibutylbenzimidazolylidene silver complexes having chloride, nitrate or cyanide as an anion part through an iodide/anion exchange from N,N′-dibutylbenzimidazolium iodide are described, representing a practical route to benzimidazolylidene silver complexes from readily accessible benzimidazolium iodide. The crystal structures of N,N′-dibutylbenzimidazolylidene silver chloride, bromide, cyanide and nitrate have been determined, showing a close ligand-unsupported Ag–Ag interaction in [(NHC)2]Ag+[AgX2]− and a “T” shape geometry about the silver(I) cation in complexes of chloride, bromide and cyanide, but a nearly linear shape in the bis(N,N  ′-dibutylbenzimidazolylidene) silver complex [(NHC)2Ag]+NO3- with non-coordinating nitrate anion.

Graphical abstractAn iodide/anion exchange route to N,N′-dibutylbenzimidazolylidene silver complexes, such as chloride and cyanide, from readily available N,N′-dibutylbenzimidazolium iodide.Figure optionsDownload full-size imageDownload as PowerPoint slide