Syntheses, structures, and reactivities of (Fe-NO)6 nitrosyls derived from polypyridine-carboxamide ligands: photoactive NO-donors and reagents for S-nitrosylation of alkyl thiols

Inorganic Chemistry
Raman K AfsharPradip K Mascharak

Abstract

Two new iron nitrosyls derived from two designed pentadentate ligands N,N-bis(2-pyridylmethyl)-amine-N'-(2-pyridylmethyl)acetamide and N,N-bis(2-pyridylmethyl)-amine-N'-[1-(2-pyridinyl)ethyl]acetamide (PcPy(3)H and MePcPy(3)H, respectively, where H is the dissociable amide proton) have been structurally characterized. These complexes are similar to a previously reported (Fe-NO)6 complex, [(PaPy(3))Fe(NO)](ClO(4))(2) (1) that releases NO under mild conditions. The present nitrosyls, namely [(PcPy(3))Fe(NO)](ClO(4))(2) (2) and [(MePcPy(3))Fe(NO)](ClO(4))(2) (3), belong to the same (Fe-NO)6 family and exhibit (a) clean (1)H NMR spectra in CD(3)CN indicating S = 0 ground state, (b) almost linear Fe-N-O angles (177.3(5) degrees and 177.6(4) degrees for 2 and 3, respectively), and (c) N-O stretching frequencies (nu(NO)) in the range 1900-1925 cm(-)(1). The binding of NO at the non-heme iron centers of 1-3 is completely reversible and all three nitrosyls rapidly release NO when exposed to light (50 W tungsten bulb). In addition to acting as photoactive NO-donors, these complexes also nitrosylate thiols such as N-acetylpenicillamine, 3-mercaptopropionic acid, and N-acetyl-cysteine-methyl-ester in yields that range from 30 to 90% in the...Continue Reading

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Citations

Sep 1, 2009·Chemical Reviews·Kathryn L Haas, Katherine J Franz
Dec 23, 2016·Journal of the American Chemical Society·James J YanEdward I Solomon
Jun 2, 2005·Journal of Inorganic Biochemistry·Raman K AfsharPradip K Mascharak
Jul 7, 2007·Physical Chemistry Chemical Physics : PCCP·Adriano ZecchinaGabriele Ricchiardi
Feb 15, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Aura A Eroy-RevelesPradip K Mascharak
Jul 25, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Bishnubasu GiriSomnath Maji
Aug 6, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Han-Hun ChangShow-Jen Chiou
Jun 9, 2005·Chemical Reviews·Konrad SzaciłowskiGrazyna Stochel
Apr 7, 2005·Journal of Inorganic Biochemistry·V K K PraneethNicolai Lehnert
Aug 10, 2007·Journal of the American Chemical Society·Jeanet ConradieAbhik Ghosh

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