The reaction of μ-η2: η2-peroxo- and bis(μ-oxo)dicopper complexes with flavonol

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Abstract

The [Cu2(μ-O)2]2+ and [Cu 2(μ-η22-O)2] 2+ motifs with coordinated N,N,N-tribenzyl-1,4,7-triazacyclononane and N,N,N-triisopropyl-1,4,7-triazacyclononane auxiliary ligands in their reaction with flavonol do not lead to ring scission products of the heterocycle, but the formation of the corresponding (flavonolato)copper(II) complexes [Cu(fla)(Bz-TAC)]ClO4 and [Cu(fla)(iPr-TAC)]ClO4. The subsequent oxygenolysis of the coordinated flavonolate ligand leads to O-benzoylsalicylate at elevated temperature, resulting in the enzyme mimicking products [Cu(O-bs)(Bz-TAC)]ClO4, [Cu(O-bs)(iPr-TAC)]ClO4) as well as carbon monoxide. The X-ray structures of [Cu(fla)(Bz-TAC)]ClO 4, [Cu(O-bs)(Bz-TAC)]ClO4, and [Cu(O-bs)(iPr-TAC)]ClO 4) are presented.

Original languageEnglish
Pages (from-to)2253-2259
Number of pages7
JournalEuropean Journal of Inorganic Chemistry
Issue number11
DOIs
Publication statusPublished - Jun 7 2004

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Ligands
Carbon Monoxide
Copper
3-hydroxyflavone
perchlorate
X rays
Enzymes
Temperature
1,4,7-triazacyclononane

Keywords

  • Copper
  • Flavonol
  • Model compounds
  • Oxygen
  • Quercetinase

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

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title = "The reaction of μ-η2: η2-peroxo- and bis(μ-oxo)dicopper complexes with flavonol",
abstract = "The [Cu2(μ-O)2]2+ and [Cu 2(μ-η2:η2-O)2] 2+ motifs with coordinated N,N,N-tribenzyl-1,4,7-triazacyclononane and N,N,N-triisopropyl-1,4,7-triazacyclononane auxiliary ligands in their reaction with flavonol do not lead to ring scission products of the heterocycle, but the formation of the corresponding (flavonolato)copper(II) complexes [Cu(fla)(Bz-TAC)]ClO4 and [Cu(fla)(iPr-TAC)]ClO4. The subsequent oxygenolysis of the coordinated flavonolate ligand leads to O-benzoylsalicylate at elevated temperature, resulting in the enzyme mimicking products [Cu(O-bs)(Bz-TAC)]ClO4, [Cu(O-bs)(iPr-TAC)]ClO4) as well as carbon monoxide. The X-ray structures of [Cu(fla)(Bz-TAC)]ClO 4, [Cu(O-bs)(Bz-TAC)]ClO4, and [Cu(O-bs)(iPr-TAC)]ClO 4) are presented.",
keywords = "Copper, Flavonol, Model compounds, Oxygen, Quercetinase",
author = "J. Kaizer and J. Pap and G. Speier and L. P{\'a}rk{\'a}ny{\'i}",
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T1 - The reaction of μ-η2

T2 - η2-peroxo- and bis(μ-oxo)dicopper complexes with flavonol

AU - Kaizer, J.

AU - Pap, J.

AU - Speier, G.

AU - Párkányí, L.

PY - 2004/6/7

Y1 - 2004/6/7

N2 - The [Cu2(μ-O)2]2+ and [Cu 2(μ-η2:η2-O)2] 2+ motifs with coordinated N,N,N-tribenzyl-1,4,7-triazacyclononane and N,N,N-triisopropyl-1,4,7-triazacyclononane auxiliary ligands in their reaction with flavonol do not lead to ring scission products of the heterocycle, but the formation of the corresponding (flavonolato)copper(II) complexes [Cu(fla)(Bz-TAC)]ClO4 and [Cu(fla)(iPr-TAC)]ClO4. The subsequent oxygenolysis of the coordinated flavonolate ligand leads to O-benzoylsalicylate at elevated temperature, resulting in the enzyme mimicking products [Cu(O-bs)(Bz-TAC)]ClO4, [Cu(O-bs)(iPr-TAC)]ClO4) as well as carbon monoxide. The X-ray structures of [Cu(fla)(Bz-TAC)]ClO 4, [Cu(O-bs)(Bz-TAC)]ClO4, and [Cu(O-bs)(iPr-TAC)]ClO 4) are presented.

AB - The [Cu2(μ-O)2]2+ and [Cu 2(μ-η2:η2-O)2] 2+ motifs with coordinated N,N,N-tribenzyl-1,4,7-triazacyclononane and N,N,N-triisopropyl-1,4,7-triazacyclononane auxiliary ligands in their reaction with flavonol do not lead to ring scission products of the heterocycle, but the formation of the corresponding (flavonolato)copper(II) complexes [Cu(fla)(Bz-TAC)]ClO4 and [Cu(fla)(iPr-TAC)]ClO4. The subsequent oxygenolysis of the coordinated flavonolate ligand leads to O-benzoylsalicylate at elevated temperature, resulting in the enzyme mimicking products [Cu(O-bs)(Bz-TAC)]ClO4, [Cu(O-bs)(iPr-TAC)]ClO4) as well as carbon monoxide. The X-ray structures of [Cu(fla)(Bz-TAC)]ClO 4, [Cu(O-bs)(Bz-TAC)]ClO4, and [Cu(O-bs)(iPr-TAC)]ClO 4) are presented.

KW - Copper

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KW - Model compounds

KW - Oxygen

KW - Quercetinase

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