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• W2919860570 abstract "The amide functional group is a fundamental building block of proteins, but is also present in several industrial chemicals such as acetamide and acrylamide. Some acetamide derivatives are known to deplete cytoplasmic heme, and some acrylamide derivatives are known to cause porphyria and may activate soluble guanylyl cyclase through a heme-dependent mechanism. We have prepared a representative set of six-coordinate acetamide and acrylamide (L) complexes of iron porphyrins of the form [(por)Fe(L)2]ClO4 (por = TPP (tetraphenylporphyrinato dianion), T(p-OMe)PP (tetrakis(p-methoxyphenyl)porphyrinato dianion)) in 76–83% yields. We have also prepared the five-coordinate derivatives [(OEP)Fe(L)]ClO4 (OEP = octaethylporphyrinato dianion) in 68–75% yields. These compounds were characterized by IR spectroscopy and by single-crystal X-ray crystallography. The molecular structures reveal the monodentate O-binding of the acetamide and acrylamide ligands to the ferric centers, with variable H-bonding exhibited between the acetamide/acrylamide –NH2 moieties and the perchlorate anions. The five-coordinate OEP derivatives exhibit a π-π stacking of their porphyrin macrocycles, with the acetamide complex in the Class I and the acrylamide complex in the Class S groups. These compounds represent the first structurally characterized acetamide and acrylamide adducts of iron porphyrins. Reactions of the six-coordinate derivatives with NO result in the nitrosyl [(por)Fe(NO)(L)]ClO4 derivatives that have been characterized by IR spectroscopy." @default.
• W2919860570 created "2019-03-11" @default.
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• W2919860570 date "2019-05-01" @default.
• W2919860570 modified "2023-10-11" @default.
• W2919860570 title "Interactions of acetamide and acrylamide with heme models: Synthesis, infrared spectra, and solid state molecular structures of five- and six-coordinate ferric porphyrin derivatives" @default.
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• W2919860570 doi "https://doi.org/10.1016/j.jinorgbio.2019.03.003" @default.
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• W2919860570 hasPublicationYear "2019" @default.
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