Interactions of acetamide and acrylamide with heme models: Synthesis, infrared spectra, and solid state molecular structures of five- and six-coordinate ferric porphyrin derivatives.

摘要: Abstract The amide functional group is a fundamental building block of proteins, but also present in several industrial chemicals such as acetamide and acrylamide. Some derivatives are known to deplete cytoplasmic heme, some acrylamide cause porphyria may activate soluble guanylyl cyclase through heme-dependent mechanism. We have prepared representative set six-coordinate (L) complexes iron porphyrins the form [(por)Fe(L)2]ClO4 (por = TPP (tetraphenylporphyrinato dianion), T(p-OMe)PP (tetrakis(p-methoxyphenyl)porphyrinato dianion)) 76–83% yields. five-coordinate [(OEP)Fe(L)]ClO4 (OEP = octaethylporphyrinato dianion) 68–75% These compounds were characterized by IR spectroscopy single-crystal X-ray crystallography. molecular structures reveal monodentate O-binding ligands ferric centers, with variable H-bonding exhibited between acetamide/acrylamide –NH2 moieties perchlorate anions. OEP exhibit π-π stacking their porphyrin macrocycles, complex Class I S groups. represent first structurally adducts porphyrins. Reactions NO result nitrosyl [(por)Fe(NO)(L)]ClO4 that been spectroscopy.