Coordination chemistry of acrylamide

This review provides a literature survey of the coordination chemistry of acrylamide, CH2=CHC(O)NH2 (also known as 2-propenamide, =AAm), with a variety of transition metals. First, a general overview of the structure and possible modes of coordination of acrylamide are discussed. This is followed by a summary of the published data on the syntheses and structures of acrylamide complexes. Despite the potential versatility of acrylamide as a ligand, only few complexes that coordinate exclusively through the carbonyl oxygen, [Co(AAm)(4)(H2O)(2)](NO3)(2), [Cu(AAM)(4)(NO3)(2)], [Co(AAm)(4)Cl-2], and [Co(AAm)(6)][CoCl4] have been fully characterized by spectroscopic and X-ray diffraction studies. Finally, some reactions involving acrylamide or acrylamide-based ligands coordinated with less acidic biologically relevant transition metals are considered in order to form a notion of the potential role of such interactions in acrylamide reactivity in biological systems. With regard to acrylamide in food and its health effects, the solution and solid-state chemistry of acrylamide or acrylamide-based ligands (metabolites) with less acidic biologically relevant metal ions may be of a great relevance in elucidating the mechanism of acrylamide metabolism and its health effects. (c) 2005 Elsevier B.V. All rights reserved.