Biochemistry, Chemistry & Physics: Faculty Publications
A Copper(II) tris-imidazolylphosphine complex as a functional model of flavonol 2,4-dioxygenase
Document Type
Article
Publication Date
6-5-2019
Publication Title
Journal of Molecular Structure
DOI
10.1016/j.molstruc.2019.02.078
Abstract
Reaction of tetrakis(acetonitrile)copper(I) perchlorate ([Cu(NCCH3)4][ClO4]), tris-1-ethyl-4-methylimidazolylphosphine (T1Et4MeIP) (1) and 3-hydroxyflavone (flavH) under ambient conditions produces an in-situ generated flavonol bound copper(II) complex, which converts to a stable green complex that formulates to [Cu(T1Et4MeIP)(flav)][ClO4] (2). The crystal structure of 2 was determined by X-ray diffraction and crystallizes in a triclinic system (P) with unit cell dimensions of a = 14.537(15) Å, b = 15.794(14) Å, c = 17.044(17) Å, α = 65.58(3)˚, β = 86.80(5)˚, γ = 73.34(4)˚, V = 3376(6) Å3 and Z = 2. While the five-coordinate copper(II) complex is stable under ambient conditions in the solid state, it undergoes oxidative scission of the flavonol pyrone ring under photolytic (300 nm) and/or thermal (120 °C) conditions in the presence of molecular oxygen. The degradative process produces the corresponding methylated products: methylbenzoate, methyl salicylate and N,N-dimethylbenzamide. In addition, the previously undisclosed single crystal X-ray structure of tris-1-ethyl-4-methylimidazolylphosphine (1), T1Et4MeIP, is also reported.
Recommended Citation
Lynch, Will E.; Gajdosik-Nivens, Delana; Quillian, Brandon; Padgett, Clifford W.; Peek, Nathan; Petrillo, Anthony; and Stone, John W., "A Copper(II) tris-imidazolylphosphine complex as a functional model of flavonol 2,4-dioxygenase" (2019). Biochemistry, Chemistry & Physics: Faculty Publications. 3.
https://digitalcommons.georgiasouthern.edu/bcp-facpubs/3
Copyright
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Comments
Georgia Southern University faculty members, Will E. Lynch, Delana Gajdosik-Nivens, Brandon Quilian, Clifford W. Padgett, and John W. Stone co-authored "A Copper(II) Tris-imidazolylphosphine Complex as a Structural and Functional Model of Flavonol 2,4-Dioxygenase."