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Dioxygen reactivity of iron(ii)-gentisate/1,4-dihydroxy-2-naphthoate complexes of N4 ligands: Oxidative coupling of 1,4-dihydroxy-2-naphthoate

Dalton Transactions, ISSN: 1477-9234, Vol: 48, Issue: 45, Page: 16993-17004
2019
  • 2
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  • 9
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  • Citations
    2
    • Citation Indexes
      2
  • Captures
    9
  • Social Media
    54
    • Shares, Likes & Comments
      54
      • Facebook
        54

Article Description

The influence of supporting ligands and co-ligands on the dioxygen reactivity of a series of iron(ii) complexes, [(6-Me-TPA)Fe(GN-H)] (1), [(6-Me-TPA)Fe(DHN-H)] (1a), [(BPMEN)Fe(GN-H)] (2), [(BPMEN)Fe(DHN-H)] (2a), [(TBimA)Fe(GN-H)] (3), and [(TBimA)Fe(DHN-H)] (3a) (GN-H = 2,5-dihydroxybenzoic acid and DHN-H = 1,4-dihydroxy-2-naphthoic acid) of N4 ligands, is presented. The iron(ii)-gentisate complexes react with dioxygen to afford the corresponding iron(iii) species. On the contrary, DHN-H undergoes oxidative C-C coupling to form [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3-hydroxy-3′-carboxylic acid (BNTHC) on 1a, and [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3,3′-dicarboxylic acid (BNTD) on 2a and 3a. In each case, the reaction proceeds through an iron(iii)-DHN species. The X-ray single crystal structures of [(6-Me-TPA)Fe(BNTD)] (1) and [(BPMEN)Fe(BNTD)] (2) confirm the coupling of two DHN-H molecules. The formation of iron(iii) product without any coupling of co-ligand from the complexes, [(BPMEN)Fe(HNA)] (2b) and [(BPMEN)Fe(5-OMeSA)] (2c) (HNA = 1-hydroxy-2-naphthoate, 5-OMeSA = 5-methoxysalicylate) confirms the importance of para-hydroxy group for the coupling reaction. The unusual coupling of DHN-H by the iron(ii) complexes of the neutral N4 ligands is distinctly different from the oxygenolytic aromatic C-C cleavage of DHN by the iron(ii) complex of a facial N3 ligand.

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