Preparation and oxygenation of (flavonolato)copper isoindoline complexes with relevance to quercetin dioxygenase

E. Balogh-Hergovich, J. Kaizer, G. Speier, Gottfried Huttner, Albrecht Jacobi

Research output: Contribution to journalArticle

94 Citations (Scopus)

Abstract

Mesitylcopper reacts with flavonol (flaH) in the presence of 1,3-bis(2-pyridylimino)isoindoline (indH) to yield the diamagnetic complex Cu(I)(fla)(indH), which on reaction with molecular oxygen undergoes oxidative splitting of the C2 - C3 bond of the pyranone ring of the flavonolate ligand to give Cu(I)(indH)(O-bs) (O-bs = O-benzoylsalicylate) (orthorhombic, P1, a = 8.048(7) Å, b = 8.969(9) Å, c = 19.240(2) Å, α = 85.69°, β = 80.24(7)°, γ = 77.87(7)°, V = 1337(2) Å3, Z = 2) and carbon monoxide. The reaction of [Cu(I)(CH3CN)4]ClO4, flaH, and indH with dioxygen at room temperature affords the paramagnetic complex [Cu(II)(fla)(indH)]ClO4 (υ = 2.10 υ(B)), and after elimination of HClO4, Cu(II)(fla)(ind) (orthorhombic, P(bca,) a = 8.888(2) Å, b = 19.169(7) Å, c = 33.614(10) Å, α = β = γ = 90°, V = 5727(3) Å3, Z = 8) with υ = 1.86 υ(B) is formed. The latter undergoes cleavage of the pyranone ring on oxygenation at 80 °C to give Cu(II)(ind)(O-bs) (υ = 1.87 υ(B), v(CO) = 1742 cm-1, and v(CO2) = 1581, 1387 cm-1) and carbon monoxide. Cu(II)(fla)(ind) and [Cu(II)(fla)(indH)]ClO4 serve as good catalysts for the oxygenation of flavonol to O-benzoylsalicylic acid.

Original languageEnglish
Pages (from-to)4224-4229
Number of pages6
JournalInorganic Chemistry
Volume39
Issue number19
DOIs
Publication statusPublished - Sep 18 2000

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Dioxygenases
Oxygenation
oxygenation
Quercetin
Carbon Monoxide
carbon monoxide
Copper
copper
preparation
rings
cleavage
elimination
Molecular oxygen
catalysts
ligands
acids
room temperature
oxygen
Oxygen
Ligands

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Preparation and oxygenation of (flavonolato)copper isoindoline complexes with relevance to quercetin dioxygenase. / Balogh-Hergovich, E.; Kaizer, J.; Speier, G.; Huttner, Gottfried; Jacobi, Albrecht.

In: Inorganic Chemistry, Vol. 39, No. 19, 18.09.2000, p. 4224-4229.

Research output: Contribution to journalArticle

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title = "Preparation and oxygenation of (flavonolato)copper isoindoline complexes with relevance to quercetin dioxygenase",
abstract = "Mesitylcopper reacts with flavonol (flaH) in the presence of 1,3-bis(2-pyridylimino)isoindoline (indH) to yield the diamagnetic complex Cu(I)(fla)(indH), which on reaction with molecular oxygen undergoes oxidative splitting of the C2 - C3 bond of the pyranone ring of the flavonolate ligand to give Cu(I)(indH)(O-bs) (O-bs = O-benzoylsalicylate) (orthorhombic, P1, a = 8.048(7) {\AA}, b = 8.969(9) {\AA}, c = 19.240(2) {\AA}, α = 85.69°, β = 80.24(7)°, γ = 77.87(7)°, V = 1337(2) {\AA}3, Z = 2) and carbon monoxide. The reaction of [Cu(I)(CH3CN)4]ClO4, flaH, and indH with dioxygen at room temperature affords the paramagnetic complex [Cu(II)(fla)(indH)]ClO4 (υ = 2.10 υ(B)), and after elimination of HClO4, Cu(II)(fla)(ind) (orthorhombic, P(bca,) a = 8.888(2) {\AA}, b = 19.169(7) {\AA}, c = 33.614(10) {\AA}, α = β = γ = 90°, V = 5727(3) {\AA}3, Z = 8) with υ = 1.86 υ(B) is formed. The latter undergoes cleavage of the pyranone ring on oxygenation at 80 °C to give Cu(II)(ind)(O-bs) (υ = 1.87 υ(B), v(CO) = 1742 cm-1, and v(CO2) = 1581, 1387 cm-1) and carbon monoxide. Cu(II)(fla)(ind) and [Cu(II)(fla)(indH)]ClO4 serve as good catalysts for the oxygenation of flavonol to O-benzoylsalicylic acid.",
author = "E. Balogh-Hergovich and J. Kaizer and G. Speier and Gottfried Huttner and Albrecht Jacobi",
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T1 - Preparation and oxygenation of (flavonolato)copper isoindoline complexes with relevance to quercetin dioxygenase

AU - Balogh-Hergovich, E.

AU - Kaizer, J.

AU - Speier, G.

AU - Huttner, Gottfried

AU - Jacobi, Albrecht

PY - 2000/9/18

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N2 - Mesitylcopper reacts with flavonol (flaH) in the presence of 1,3-bis(2-pyridylimino)isoindoline (indH) to yield the diamagnetic complex Cu(I)(fla)(indH), which on reaction with molecular oxygen undergoes oxidative splitting of the C2 - C3 bond of the pyranone ring of the flavonolate ligand to give Cu(I)(indH)(O-bs) (O-bs = O-benzoylsalicylate) (orthorhombic, P1, a = 8.048(7) Å, b = 8.969(9) Å, c = 19.240(2) Å, α = 85.69°, β = 80.24(7)°, γ = 77.87(7)°, V = 1337(2) Å3, Z = 2) and carbon monoxide. The reaction of [Cu(I)(CH3CN)4]ClO4, flaH, and indH with dioxygen at room temperature affords the paramagnetic complex [Cu(II)(fla)(indH)]ClO4 (υ = 2.10 υ(B)), and after elimination of HClO4, Cu(II)(fla)(ind) (orthorhombic, P(bca,) a = 8.888(2) Å, b = 19.169(7) Å, c = 33.614(10) Å, α = β = γ = 90°, V = 5727(3) Å3, Z = 8) with υ = 1.86 υ(B) is formed. The latter undergoes cleavage of the pyranone ring on oxygenation at 80 °C to give Cu(II)(ind)(O-bs) (υ = 1.87 υ(B), v(CO) = 1742 cm-1, and v(CO2) = 1581, 1387 cm-1) and carbon monoxide. Cu(II)(fla)(ind) and [Cu(II)(fla)(indH)]ClO4 serve as good catalysts for the oxygenation of flavonol to O-benzoylsalicylic acid.

AB - Mesitylcopper reacts with flavonol (flaH) in the presence of 1,3-bis(2-pyridylimino)isoindoline (indH) to yield the diamagnetic complex Cu(I)(fla)(indH), which on reaction with molecular oxygen undergoes oxidative splitting of the C2 - C3 bond of the pyranone ring of the flavonolate ligand to give Cu(I)(indH)(O-bs) (O-bs = O-benzoylsalicylate) (orthorhombic, P1, a = 8.048(7) Å, b = 8.969(9) Å, c = 19.240(2) Å, α = 85.69°, β = 80.24(7)°, γ = 77.87(7)°, V = 1337(2) Å3, Z = 2) and carbon monoxide. The reaction of [Cu(I)(CH3CN)4]ClO4, flaH, and indH with dioxygen at room temperature affords the paramagnetic complex [Cu(II)(fla)(indH)]ClO4 (υ = 2.10 υ(B)), and after elimination of HClO4, Cu(II)(fla)(ind) (orthorhombic, P(bca,) a = 8.888(2) Å, b = 19.169(7) Å, c = 33.614(10) Å, α = β = γ = 90°, V = 5727(3) Å3, Z = 8) with υ = 1.86 υ(B) is formed. The latter undergoes cleavage of the pyranone ring on oxygenation at 80 °C to give Cu(II)(ind)(O-bs) (υ = 1.87 υ(B), v(CO) = 1742 cm-1, and v(CO2) = 1581, 1387 cm-1) and carbon monoxide. Cu(II)(fla)(ind) and [Cu(II)(fla)(indH)]ClO4 serve as good catalysts for the oxygenation of flavonol to O-benzoylsalicylic acid.

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