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Transformation of [{(NO)<jats:sub>2<\/jats:sub>Fe(\u03bc\u2010S<jats:italic>t<\/jats:italic>Bu)}<jats:sub>2<\/jats:sub>] (<jats:bold>1<jats:italic>\u2010t<\/jats:italic>BuS<\/jats:bold>) into the {Fe(NO)<jats:sub>2<\/jats:sub>}<jats:sup>9<\/jats:sup> DNIC [(NO)<jats:sub>2<\/jats:sub>Fe(S<jats:italic>t<\/jats:italic>Bu)(MeIm)] (<jats:bold>2\u2010MeIm<\/jats:bold>) occurs under addition of 20\u2005equiv of 1\u2010methylimidazole (MeIm) into a solution of <jats:bold>1<jats:italic>\u2010t<\/jats:italic>BuS<\/jats:bold> in THF. The dynamic interconversion between {Fe(NO)<jats:sub>2<\/jats:sub>}<jats:sup>9<\/jats:sup> [(NO)<jats:sub>2<\/jats:sub>Fe(S\u2010NAP)(dmso)] (<jats:bold>2\u2010dmso<\/jats:bold>) (NAP=<jats:italic>N<\/jats:italic>\u2010acetyl\u2010<jats:sc>D<\/jats:sc>\u2010penicillamine) and [{(NO)<jats:sub>2<\/jats:sub>Fe(\u03bc\u2010S\u2010NAP)}<jats:sub>2<\/jats:sub>] (<jats:bold>1\u2010NAP<\/jats:bold>) was also observed in a solution of complex <jats:bold>1\u2010NAP<\/jats:bold> in DMSO. In contrast to the reaction of complex <jats:bold>2\u2010MeIm<\/jats:bold> and bis(dimethylthiocarbamoyl) disulfide ((DTC)<jats:sub>2<\/jats:sub>) to yield {Fe(NO)}<jats:sup>7<\/jats:sup> [(NO)Fe(DTC)<jats:sub>2<\/jats:sub>] (<jats:bold>3<\/jats:bold>) (DTC=S<jats:sub>2<\/jats:sub>CNMe<jats:sub>2<\/jats:sub>) accompanied by (<jats:italic>t<\/jats:italic>BuS)<jats:sub>2<\/jats:sub> and NO<jats:sub>(g)<\/jats:sub>, transformation of {Fe(NO)<jats:sub>2<\/jats:sub>}<jats:sup>9<\/jats:sup> <jats:bold>2\u2010MeIm<\/jats:bold> (<jats:bold>2\u2010dmso<\/jats:bold>) into RSNOs (RS=<jats:italic>t<\/jats:italic>BuS, NAP\u2010S) along with complex <jats:bold>3<\/jats:bold> induced by the Br\u00f8nsted acid solution of (DTC)<jats:sub>2<\/jats:sub> demonstrated that Br\u00f8nsted acid may play a critical role in triggering S\u2010nitrosation of the coordinated thiolate of DNICs <jats:bold>2\u2010MeIm<\/jats:bold> (or <jats:bold>2\u2010dmso<\/jats:bold>) to produce RSNOs. That is, DNIC\u2010mediated S\u2010nitrosation requires a Br\u00f8nsted acid\u2013Lewis base pair to produce RSNO. Transformation of DNICs into RSNOs may only occur on the one\u2010thiolate\u2010containing {Fe(NO)<jats:sub>2<\/jats:sub>}<jats:sup>9<\/jats:sup> DNICs, in contrast to protonation of the two\u2010thiolate\u2010containing DNICs [(NO)<jats:sub>2<\/jats:sub>Fe(SR)<jats:sub>2<\/jats:sub>]<jats:sup>\u2212<\/jats:sup> by Br\u00f8nsted acid to yield [{(NO)<jats:sub>2<\/jats:sub>Fe(\u03bc\u2010SR)}<jats:sub>2<\/jats:sub>]. These results might rationalize that the known protein\u2010Cys\u2010SNO sites derived from DNICs were located adjacent to acid and base motifs, and no protein\u2010bound SNO characterized to date has been directly derived from [protein\u2013(cysteine)<jats:sub>2<\/jats:sub>Fe(NO)<jats:sub>2<\/jats:sub>] in biology.<\/jats:p>","DOI":"10.1002\/chem.201100253","type":"journal-article","created":{"date-parts":[[2011,10,18]],"date-time":"2011-10-18T03:24:29Z","timestamp":1318908269000},"page":"13358-13366","source":"Crossref","is-referenced-by-count":38,"title":["Transformation of the {Fe(NO)<sub>2<\/sub>}<sup>9<\/sup> Dinitrosyl Iron Complexes (DNICs) into <i>S<\/i>\u2010Nitrosothiols (RSNOs) Triggered by Acid\u2013Base 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