Bioinspired oxidation of oximes to nitric oxide with dioxygen by a nonheme iron(II) complex

Shrabanti Bhattacharya, Triloke Ranjan Lakshman, Subhankar Sutradhar, Chandan Kumar Tiwari, Tapan Kanti Paine

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The ability of two iron(II) complexes, [(TpPh2)FeII(benzilate)] (1) and [(TpPh2)(FeII)2(NPP)3] (2) (TpPh2 = hydrotris(3,5-diphenylpyrazol-1-yl)borate, NPP-H = α-isonitrosopropiophenone), of a monoanionic facial N3 ligand in the O2-dependent oxidation of oximes is reported. The mononuclear complex 1 reacts with dioxygen to decarboxylate the iron-coordinated benzilate. The oximate-bridged dinuclear complex (2), which contains a high-spin (TpPh2)FeII unit and a low-spin iron(II)–oximate unit, activates dioxygen at the high-spin iron(II) center. Both the complexes exhibit the oxidative transformation of oximes to the corresponding carbonyl compounds with the incorporation of one oxygen atom from dioxygen. In the oxidation process, the oxime units are converted to nitric oxide (NO) or nitroxyl (HNO). The iron(II)–benzilate complex (1) reacts with oximes to afford HNO, whereas the iron(II)–oximate complex (2) generates NO. The results described here suggest that the oxidative transformation of oximes to NO/HNO follows different pathways depending upon the nature of co-ligand/reductant.

Original languageEnglish
Pages (from-to)3-11
Number of pages9
JournalJournal of Biological Inorganic Chemistry
Volume25
Issue number1
DOIs
StatePublished - 1 Feb 2020
Externally publishedYes

Keywords

  • Iron
  • Nitric oxide
  • Nonheme
  • Oxidation
  • Oximes

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

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