Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Phenolate-bonded bis(μ-oxido)-bis-copper( iii ) intermediates: hydroxylation and dehalogenation reactivities

Journal Article · · Faraday Discussions
DOI:https://doi.org/10.1039/d1fd00071c· OSTI ID:1982205
 [1];  [1];  [1];  [1];  [2];  [1]
  1. Department of Chemistry, Stanford University, Stanford, California 94305, USA
  2. Department of Chemistry and Biochemistry, California State University, Chico, California 95929, USA
+ Show Author Affiliations

A Cu(iii) intermediate, ADBPD, effects novel dehalogenation–hydroxylations of exogenous phenolates; it is best formulated as containing 2 phenolates/Cu2O2core.

Research Organization:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC02-76SF00515
OSTI ID:
1982205
Journal Information:
Faraday Discussions, Vol. 234, Issue 0; ISSN 1359-6640
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English

References (55)

Multicopper Oxidases and Oxygenases journal January 1996
How Does Tyrosinase Work? Recent Insights from Model Chemistry and Structural Biology journal May 2000
Crystallographic Evidence That the Dinuclear Copper Center of Tyrosinase Is Flexible during Catalysis journal January 2006
Trapping tyrosinase key active intermediate under turnover journal January 2009
Substrate and Lewis Acid Coordination Promote O–O Bond Cleavage of an Unreactive L 2 Cu II 2 (O 2 2– ) Species to Form L 2 Cu III 2 (O) 2 Cores with Enhanced Oxidative Reactivity journal February 2017
.mu.-.eta.2:.eta.2-Peroxo binuclear copper complex, [Cu(HB(3,5-(Me2CH)2pz)3)]2(O2) journal November 1989
Structure and Spectroscopy of Copper−Dioxygen Complexes journal February 2004
Reactivity of Dioxygen−Copper Systems journal February 2004
A New Intermediate in Copper Dioxygen Chemistry: Breaking the O-O Bond To Form a {Cu2(.mu.-O)2}2+ Core journal August 1995
Exogenous Substrate Reactivity with a [Cu(III) 2 O 2 ] 2+ Core:  Structural Implications journal June 1999
Reactivity of Copper(I) Complexes Towards Dioxygen journal November 2000
Structure and O2-reactivity of copper(i) complexes supported by pyridylalkylamine ligands journal January 2006
Copper–Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity journal January 2017
Reversible Cleavage and Formation of the Dioxygen O-O Bond Within a Dicopper Complex journal March 1996
Differential Reactivity between Interconvertible Side-On Peroxo and Bis- μ -oxodicopper Isomers Using Peralkylated Diamine Ligands journal September 2000
Syntheses, Structures, and O2-Reactivities of Copper(I) Complexes with Bis(2-pyridylmethyl)amine and Bis(2-quinolylmethyl)amine Tridentate Ligands journal November 2006
Reversible Dioxygen Binding and Phenol Oxygenation in a Tyrosinase Model System journal February 2000
Effects of Metal Ions on Physicochemical Properties and Redox Reactivity of Phenolates and Phenoxyl Radicals: Mechanistic Insight into Hydrogen Atom Abstraction by Phenoxyl Radical−Metal Complexes journal February 2001
The phenol ortho-oxygenation by mononuclear copper(i) complexes requires a dinuclear µ-η2∶η2-peroxodicopper(ii) complex rather than mononuclear CuO2 species journal February 2003
Hydroxylation of Phenolic Compounds by a Peroxodicopper(II) Complex:  Further Insight into the Mechanism of Tyrosinase journal December 2005
Tyrosinase Reactivity in a Model Complex: An Alternative Hydroxylation Mechanism journal June 2005
Reaction Coordinate of a Functional Model of Tyrosinase: Spectroscopic and Computational Characterization journal April 2009
Tyrosinase-Like Reactivity in a CuIII2(μ-O)2 Species journal April 2008
Selective Ortho -Hydroxylation-Defluorination of 2-Fluorophenolates with a Bis(μ-oxo)dicopper(III) Species journal July 2014
O2 Activation and Selective Phenolate ortho Hydroxylation by an Unsymmetric Dicopper μ-η1:η1-Peroxido Complex journal February 2010
Simplest Monodentate Imidazole Stabilization of the oxy-Tyrosinase Cu 2 O 2 Core: Phenolate Hydroxylation through a Cu III Intermediate journal July 2016
Theoretical study of the hydroxylation of phenols mediated by an end-on bound superoxo–copper(II) complex journal November 2008
Mechanistic Insights into the ortho-Defluorination-Hydroxylation of 2-Halophenolates Promoted by a Bis(μ-oxo)dicopper(III) Complex journal November 2020
A Stabilized μ-η2:η2 Peroxodicopper(II) Complex with a Secondary Diamine Ligand and Its Tyrosinase-like Reactivity journal July 2002
Electronic structure of peroxide bridged copper dimers of relevance to oxyhemocyanin journal July 1990
An electronic structural comparison of copper-peroxide complexes of relevance to hemocyanin and tyrosinase active sites journal April 1991
Oxygen Binding, Activation, and Reduction to Water by Copper Proteins journal December 2001
Copper Active Sites in Biology journal January 2014
μ-η 2 :η 2 -Peroxodicopper(II) Complex with a Secondary Diamine Ligand:  A Functional Model of Tyrosinase journal March 2006
Spectroscopic and Electronic Structural Studies of the Cu(III) 2 Bis-μ-oxo Core and Its Relation to the Side-On Peroxo-Bridged Dimer journal October 1999
A Systematic K-edge X-ray Absorption Spectroscopic Study of Cu(III) Sites journal June 2000
Reversible Dioxygen Binding and Aromatic Hydroxylation in O2-Reactions with Substituted Xylyl Dinuclear Copper(I) Complexes: Syntheses and Low-Temperature Kinetic/Thermodynamic and Spectroscopic Investigations of a Copper Monooxygenase Model System journal February 1994
Binucleating Ligand Structural Effects on (μ-Peroxo)- and Bis(μ-oxo)dicopper Complex Formation and Decay:  Competition between Arene Hydroxylation and Aliphatic C−H Bond Activation journal December 1997
Kinetic Evaluation of Phenolase Activity of Tyrosinase Using Simplified Catalytic Reaction System journal October 2003
Dioxygen Activation by Copper Complexes. Mechanistic Insights into Copper Monooxygenases and Copper Oxidases journal October 2002
Theoretical Study of the Oxidation of Phenolates by the [Cu2O2(N,N′-di-tert-butylethylenediamine)2]2+Complex journal January 2013
Natural transition orbitals journal March 2003
Complexity with simplicity: a steric continuum of chelating diamines with copper( i ) and dioxygen journal January 2003
β-Diketiminate Ligand Backbone Structural Effects on Cu(I)/O2 Reactivity:  Unique Copper−Superoxo and Bis(μ-oxo) Complexes journal February 2002
Phenolate Hydroxylation in a Bis(μ-oxo)dicopper(III) Complex: Lessons from the Guanidine/Amine Series journal January 2009
Reversible O−O Bond Cleavage in Copper−Dioxygen Isomers:  Impact of Anion Basicity journal July 2006
Formation of a Bridged Butterfly-Type μ-η2:η2-Peroxo Dicopper Core Structure with a Carboxylate Group journal November 2008
Copper(II) Hexaaza Macrocyclic Binuclear Complexes Obtained from the Reaction of Their Copper(I) Derivates and Molecular Dioxygen journal April 2006
Dioxygen-copper reactivity: intermediacy of a peroxo-dicopper(II) (dioxygen-copper) complex in the hydroxylation reaction of a model mono-oxygenase system journal December 1986
Oxidative dehalogenation during a copper complex mediated hydroxylation reaction journal October 1990
Bacterial dehalogenation journal December 1998
Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product journal September 1993
Bacterial dehalogenases: biochemistry, genetics, and biotechnological applications journal December 1994
Effect of Various Factors on Dehalogenation of Chlorinated Phenols and Anilines during Oxidative Coupling journal March 1995
Dehalogenation of Xenobiotics as a Consequence of Binding to Humic Materials journal May 2000

Similar Records

Related Subjects

Chemistry