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Title: Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized CuII bis-phenoxide complex

Abstract

Here, the tetradentate mixed imino/amino phenoxide ligand (N-(3,5-di-tert-butylsalicylidene)-N'-(2-hydroxyl-3,5-di-tert-butylbenzyl))-trans-1,2-cyclohexanediamine (salalen) was complexed with CuII, and the resulting Cu complex (2) was characterized by a number of experimental techniques and theoretical calculations. Two quasi-reversible redox processes for 2, as observed by cyclic voltammetry, demonstrated the potential stability of oxidized forms, and also the increased electron-donating ability of the salalen ligand in comparison to the salen analogue. The electronic structure of the one-electron oxidized [2]+ was studied in detail, and Cu K-edge X-ray Absorption Spectroscopy (XAS) measurements confirmed a CuII-phenoxyl radical complex in solution. Resonance Raman (rR) and variable temperature 1H NMR studies, coupled with theoretical calculations, showed that [2]+ is a triplet (S = 1) CuII-phenoxyl radical species, with localization of the radical on the more electron-rich aminophenoxide. Attempted isolation of X-ray quality crystals of [2]+ afforded [2H]+, with a protonated phenol bonded to CuII, and an additional H-bonding interaction with the SbF6 counterion. Stoichiometric reaction of dilute solutions of [2]+ with benzyl alcohol showed that the complex reacts in a similar manner as the oxidized CuII-salen analogue, and does not exhibit a substrate-binding pre-equilibrium as observed for the oxidized bis-aminophenoxide CuII-salan derivative.

Authors:
 [1];  [2];  [3];  [4];  [5];  [6]
  1. Stanford Univ., Stanford, CA (United States); Univ. of the Fraser Valley, Abbotsford, BC (Canada)
  2. California State Univ., Chico, CA (United States)
  3. Ibaraki Univ., Mito (Japan)
  4. The Univ. of Minnesota, Minneapolis, MN (United States)
  5. Simon Fraser Univ., Burnaby, BC (Canada)
  6. Stanford Univ., Stanford, CA (United States)
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1469090
Alternate Identifier(s):
OSTI ID: 1702083
Grant/Contract Number:  
AC02-76SF00515
Resource Type:
Accepted Manuscript
Journal Name:
Inorganica Chimica Acta
Additional Journal Information:
Journal Volume: 481; Journal Issue: C; Journal ID: ISSN 0020-1693
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Chiang, Linus, Wasinger, Erik C., Shimazaki, Yuichi, Young, Jr., Victor, Storr, Tim, and Stack, T. Daniel P. Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized CuII bis-phenoxide complex. United States: N. p., 2017. Web. doi:10.1016/j.ica.2017.09.042.
Chiang, Linus, Wasinger, Erik C., Shimazaki, Yuichi, Young, Jr., Victor, Storr, Tim, & Stack, T. Daniel P. Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized CuII bis-phenoxide complex. United States. https://doi.org/10.1016/j.ica.2017.09.042
Chiang, Linus, Wasinger, Erik C., Shimazaki, Yuichi, Young, Jr., Victor, Storr, Tim, and Stack, T. Daniel P. Mon . "Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized CuII bis-phenoxide complex". United States. https://doi.org/10.1016/j.ica.2017.09.042. https://www.osti.gov/servlets/purl/1469090.
@article{osti_1469090,
title = {Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized CuII bis-phenoxide complex},
author = {Chiang, Linus and Wasinger, Erik C. and Shimazaki, Yuichi and Young, Jr., Victor and Storr, Tim and Stack, T. Daniel P.},
abstractNote = {Here, the tetradentate mixed imino/amino phenoxide ligand (N-(3,5-di-tert-butylsalicylidene)-N'-(2-hydroxyl-3,5-di-tert-butylbenzyl))-trans-1,2-cyclohexanediamine (salalen) was complexed with CuII, and the resulting Cu complex (2) was characterized by a number of experimental techniques and theoretical calculations. Two quasi-reversible redox processes for 2, as observed by cyclic voltammetry, demonstrated the potential stability of oxidized forms, and also the increased electron-donating ability of the salalen ligand in comparison to the salen analogue. The electronic structure of the one-electron oxidized [2]+ was studied in detail, and Cu K-edge X-ray Absorption Spectroscopy (XAS) measurements confirmed a CuII-phenoxyl radical complex in solution. Resonance Raman (rR) and variable temperature 1H NMR studies, coupled with theoretical calculations, showed that [2•]+ is a triplet (S = 1) CuII-phenoxyl radical species, with localization of the radical on the more electron-rich aminophenoxide. Attempted isolation of X-ray quality crystals of [2•]+ afforded [2H]+, with a protonated phenol bonded to CuII, and an additional H-bonding interaction with the SbF6– counterion. Stoichiometric reaction of dilute solutions of [2•]+ with benzyl alcohol showed that the complex reacts in a similar manner as the oxidized CuII-salen analogue, and does not exhibit a substrate-binding pre-equilibrium as observed for the oxidized bis-aminophenoxide CuII-salan derivative.},
doi = {10.1016/j.ica.2017.09.042},
journal = {Inorganica Chimica Acta},
number = C,
volume = 481,
place = {United States},
year = {2017},
month = {9}
}

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Figures / Tables:

Fig. 1 Fig. 1: Chemical structures of Cu salen (1) Cu salalen (2), and Cu salan (3) of relevance to this work

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Works referenced in this record:

Preface: Forum on Redox-Active Ligands
journal, October 2011


Radical Ligands Confer Nobility on Base-Metal Catalysts
journal, February 2010


Redox-Active Ligands in Catalysis
journal, September 2012

  • Praneeth, Vijayendran K. K.; Ringenberg, Mark R.; Ward, Thomas R.
  • Angewandte Chemie International Edition, Vol. 51, Issue 41
  • DOI: 10.1002/anie.201204100

Redox-active ligands in catalysis
journal, January 2013

  • Luca, Oana R.; Crabtree, Robert H.
  • Chem. Soc. Rev., Vol. 42, Issue 4
  • DOI: 10.1039/C2CS35228A

The Shrinking World of Innocent Ligands: Conventionaland Non-Conventional Redox-Active Ligands
journal, January 2012


Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions
journal, January 2012

  • Lyaskovskyy, Volodymyr; de Bruin, Bas
  • ACS Catalysis, Vol. 2, Issue 2
  • DOI: 10.1021/cs200660v

Copper-tyrosyl radical enzymes
journal, April 2003


Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics
journal, November 2010


Glyoxal Oxidase from Phanerochaete chrysosporium Is a New Radical-Copper Oxidase
journal, January 1996

  • Whittaker, Mei M.; Kersten, Philip J.; Nakamura, Nobuhumi
  • Journal of Biological Chemistry, Vol. 271, Issue 2
  • DOI: 10.1074/jbc.271.2.681

Free Radical Catalysis by Galactose Oxidase
journal, June 2003


Resonance Raman evidence for tyrosine involvement in the radical site of galactose oxidase
journal, May 1989


A tyrosine-derived free radical in apogalactose oxidase.
journal, June 1990


Biologically inspired oxidation catalysis
journal, September 2008


Recent advances in phenoxyl radical complexes of salen-type ligands as mixed-valent galactose oxidase models
journal, January 2013

  • Lyons, Christopher T.; Stack, T. Daniel P.
  • Coordination Chemistry Reviews, Vol. 257, Issue 2
  • DOI: 10.1016/j.ccr.2012.06.003

Ten Years of a Biomimetic Approach to the Copper(II) Radical Site of Galactose Oxidase
journal, May 2007


A Square-Planar Nickel(II) Monoradical Complex with a Bis(salicylidene)diamine Ligand
journal, February 2007

  • Benisvy, Laurent; Kannappan, Ramu; Song, Yu-Fei
  • European Journal of Inorganic Chemistry, Vol. 2007, Issue 5
  • DOI: 10.1002/ejic.200601015

Reversible Double Oxidation and Protonation of the Non-Innocent Bridge in a Nickel(II) Salophen Complex
journal, November 2012

  • de Bellefeuille, David; Askari, Mohammad S.; Lassalle-Kaiser, Benedikt
  • Inorganic Chemistry, Vol. 51, Issue 23
  • DOI: 10.1021/ic301684h

New Insights into the Electronic Structure and Reactivity of One-Electron Oxidized Copper(II)-(Disalicylidene)diamine Complexes
journal, October 2012

  • Asami, Kazutaka; Tsukidate, Kazuaki; Iwatsuki, Satoshi
  • Inorganic Chemistry, Vol. 51, Issue 22
  • DOI: 10.1021/ic3018503

Radical Localization in a Series of Symmetric Ni II Complexes with Oxidized Salen Ligands
journal, September 2012

  • Chiang, Linus; Kochem, Amélie; Jarjayes, Olivier
  • Chemistry - A European Journal, Vol. 18, Issue 44
  • DOI: 10.1002/chem.201201410

Influence of the chelate effect on the electronic structure of one-electron oxidized group 10 metal(ii)-(disalicylidene)diamine complexes
journal, January 2011

  • Shimazaki, Yuichi; Arai, Natsumi; Dunn, Tim J.
  • Dalton Transactions, Vol. 40, Issue 11
  • DOI: 10.1039/c0dt01574a

Detailed Evaluation of the Geometric and Electronic Structures of One-Electron Oxidized Group 10 (Ni, Pd, and Pt) Metal(II)-(Disalicylidene)diamine Complexes
journal, September 2009

  • Shimazaki, Yuichi; Stack, T. Daniel P.; Storr, Tim
  • Inorganic Chemistry, Vol. 48, Issue 17
  • DOI: 10.1021/ic901003q

Defining the Electronic and Geometric Structure of One-Electron Oxidized Copper−Bis-phenoxide Complexes
journal, October 2008

  • Storr, Tim; Verma, Pratik; Pratt, Russell C.
  • Journal of the American Chemical Society, Vol. 130, Issue 46
  • DOI: 10.1021/ja804339m

The Geometric and Electronic Structure of a One-Electron-Oxidized Nickel(II) Bis(salicylidene)diamine Complex
journal, July 2007

  • Storr, Tim; Wasinger, Erik C.; Pratt, Russell C.
  • Angewandte Chemie International Edition, Vol. 46, Issue 27
  • DOI: 10.1002/anie.200701194

One-electron oxidized nickel(II) complexes of bis and tetra(salicylidene) phenylenediamine Schiff bases: from monoradical to interacting Ni(III) ions
journal, January 2009

  • Rotthaus, Olaf; Jarjayes, Olivier; Philouze, Christian
  • Dalton Transactions, Issue 10
  • DOI: 10.1039/b811702k

Up to four phenoxyl radicals coordinated to two metal ions in copper and zinc complexes?
journal, January 2007

  • Rotthaus, Olaf; Jarjayes, Olivier; Thomas, Fabrice
  • Dalton Transactions, Issue 8
  • DOI: 10.1039/b612068g

A versatile electronic hole in one-electron oxidized NiIIbis-salicylidene phenylenediamine complexes
journal, January 2007

  • Rotthaus, Olaf; Jarjayes, Olivier; Perez Del Valle, Carlos
  • Chemical Communications, Issue 43
  • DOI: 10.1039/b710027b

Valence Tautomerism in Octahedral and Square-Planar Phenoxyl–Nickel(II) Complexes: Are Imino Nitrogen Atoms Good Friends?
journal, September 2006

  • Rotthaus, Olaf; Thomas, Fabrice; Jarjayes, Olivier
  • Chemistry - A European Journal, Vol. 12, Issue 26
  • DOI: 10.1002/chem.200600258

Fine Tuning of the Oxidation Locus, and Electron Transfer, in Nickel Complexes of Pro-Radical Ligands
journal, March 2006

  • Rotthaus, Olaf; Jarjayes, Olivier; Thomas, Fabrice
  • Chemistry - A European Journal, Vol. 12, Issue 8
  • DOI: 10.1002/chem.200500915

Ligand Contributions to the Electronic Structures of the Oxidized Cobalt(II) salen Complexes
journal, September 2012

  • Kochem, Amélie; Kanso, Hussein; Baptiste, Benoit
  • Inorganic Chemistry, Vol. 51, Issue 20
  • DOI: 10.1021/ic300763t

One-Electron Oxidized Copper(II) Salophen Complexes: Phenoxyl versus Diiminobenzene Radical Species
journal, December 2011

  • Kochem, Amélie; Jarjayes, Olivier; Baptiste, Benoit
  • Chemistry - A European Journal, Vol. 18, Issue 4
  • DOI: 10.1002/chem.201102882

Syntheses and Electronic Structures of One-Electron-Oxidized Group 10 Metal(II)−(Disalicylidene)diamine Complexes (Metal = Ni, Pd, Pt)
journal, March 2007

  • Shimazaki, Yuichi; Yajima, Tatsuo; Tani, Fumito
  • Journal of the American Chemical Society, Vol. 129, Issue 9
  • DOI: 10.1021/ja067022r

One-Electron Oxidized Nickel(II)−(Disalicylidene)diamine Complex:  Temperature-Dependent Tautomerism between Ni(III)−Phenolate and Ni(II)−Phenoxyl Radical States
journal, August 2003

  • Shimazaki, Yuichi; Tani, Fumito; Fukui, Kôichi
  • Journal of the American Chemical Society, Vol. 125, Issue 35
  • DOI: 10.1021/ja035806o

Electrochemical and Spectroscopic Effects of Mixed Substituents in Bis(phenolate)–Copper(II) Galactose Oxidase Model Complexes
journal, April 2012

  • Pratt, Russell C.; Lyons, Christopher T.; Wasinger, Erik C.
  • Journal of the American Chemical Society, Vol. 134, Issue 17
  • DOI: 10.1021/ja211247f

Sulfanyl stabilization of copper-bonded phenoxyls in model complexes and galactose oxidase
journal, November 2011

  • Verma, P.; Pratt, R. C.; Storr, T.
  • Proceedings of the National Academy of Sciences, Vol. 108, Issue 46
  • DOI: 10.1073/pnas.1109931108

Spin Interaction in Octahedral Zinc Complexes of Mono- and Diradical Schiff and Mannich Bases
journal, December 2009

  • Orio, M.; Philouze, C.; Jarjayes, O.
  • Inorganic Chemistry, Vol. 49, Issue 2
  • DOI: 10.1021/ic901846u

X-Ray Structures of Copper(II) and Nickel(II) Radical Salen Complexes: The Preference of Galactose Oxidase for Copper(II)
journal, April 2010

  • Orio, Maylis; Jarjayes, Olivier; Kanso, Hussein
  • Angewandte Chemie International Edition, Vol. 49, Issue 29
  • DOI: 10.1002/anie.201001040

One-Electron Oxidation of Electronically Diverse Manganese(III) and Nickel(II) Salen Complexes: Transition from Localized to Delocalized Mixed-Valence Ligand Radicals
journal, June 2011

  • Kurahashi, Takuya; Fujii, Hiroshi
  • Journal of the American Chemical Society, Vol. 133, Issue 21
  • DOI: 10.1021/ja2016813

Detailed Geometric and Electronic Structures of a One-Electron-Oxidized Ni Salophen Complex and Its Amido Derivatives: One-Electron-Oxidized Ni Salophen Complex
journal, June 2014

  • Lecarme, Laureline; Chiang, Linus; Philouze, Christian
  • European Journal of Inorganic Chemistry, Vol. 2014, Issue 22
  • DOI: 10.1002/ejic.201402265

Double oxidation localizes spin in a Ni bis-phenoxyl radical complex
journal, January 2013

  • Dunn, Tim J.; Webb, Michael I.; Hazin, Khatera
  • Dalton Transactions, Vol. 42, Issue 11
  • DOI: 10.1039/c2dt32632a

Class III Delocalization and Exciton Coupling in a Bimetallic Bis-ligand Radical Complex
journal, June 2013

  • Dunn, Tim J.; Chiang, Linus; Ramogida, Caterina F.
  • Chemistry - A European Journal, Vol. 19, Issue 29
  • DOI: 10.1002/chem.201300798

Redox Noninnocence of the Bridge in Copper(II) Salophen and Bis(oxamato) Complexes
journal, September 2015


Chromium− and Manganese−salen Promoted Epoxidation of Alkenes
journal, May 2005

  • McGarrigle, Eoghan M.; Gilheany, Declan G.
  • Chemical Reviews, Vol. 105, Issue 5
  • DOI: 10.1021/cr0306945

Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis
journal, January 1999

  • Canali, Laetitia; Sherrington, David C.
  • Chemical Society Reviews, Vol. 28, Issue 2
  • DOI: 10.1039/a806483k

Catalytic asymmetric epoxidation of unfunctionalized olefins
journal, January 1990


Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane
journal, August 1991

  • Jacobsen, Eric N.; Zhang, Wei; Muci, Alexander R.
  • Journal of the American Chemical Society, Vol. 113, Issue 18
  • DOI: 10.1021/ja00018a068

Metal–Salen Schiff base complexes in catalysis: practical aspects
journal, January 2004


The chemistry and applications of multimetallic salen complexes
journal, January 2014

  • Clarke, Ryan M.; Storr, Tim
  • Dalton Transactions, Vol. 43, Issue 25
  • DOI: 10.1039/c4dt00591k

Intramolecular Charge Transfer and Biomimetic Reaction Kinetics in Galactose Oxidase Model Complexes
journal, July 2003

  • Pratt, Russell C.; Stack, T. Daniel P.
  • Journal of the American Chemical Society, Vol. 125, Issue 29
  • DOI: 10.1021/ja035837j

A functional model of galactose oxidase: catalytic oxidation of primary alcohols with a one-electron oxidized copper(II) complex
journal, January 1998

  • Saint-Aman, Eric; Me´nage, Ste´phane; Pierre, Jean-Louis
  • New Journal of Chemistry, Vol. 22, Issue 5
  • DOI: 10.1039/a801588k

Ligand Radical Localization in a Nonsymmetric One-Electron Oxidized NiII Bis-phenoxide Complex
journal, July 2010

  • Storr, Tim; Verma, Pratik; Shimazaki, Yuichi
  • Chemistry - A European Journal, Vol. 16, Issue 30
  • DOI: 10.1002/chem.201001401

Alternating Copolymerization of Cyclohexene Oxide with Carbon Dioxide Catalyzed by (salalen)CrCl Complexes
journal, September 2009

  • Nakano, Koji; Nakamura, Mitsuru; Nozaki, Kyoko
  • Macromolecules, Vol. 42, Issue 18
  • DOI: 10.1021/ma9012626

A Practical and Versatile Access to Dihydrosalen (Salalen) Ligands: Highly Enantioselective TitaniumIn Situ Catalysts for Asymmetric Epoxidation with Aqueous Hydrogen Peroxide
journal, October 2007

  • Berkessel, Albrecht; Brandenburg, Marc; Leitterstorf, Eva
  • Advanced Synthesis & Catalysis, Vol. 349, Issue 14-15
  • DOI: 10.1002/adsc.200700221

Isoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes
journal, July 2015

  • Talsi, Evgenii P.; Rybalova, Tatyana V.; Bryliakov, Konstantin P.
  • ACS Catalysis, Vol. 5, Issue 8
  • DOI: 10.1021/acscatal.5b01212

Effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward asymmetric nitroaldol reactions
journal, October 2014


An Efficient Method for the Preparation of Oxo Molybdenum Salalen Complexes and Their Unusual Use as Hydrosilylation Catalysts
journal, October 2009

  • Ziegler, Jeanette E.; Du, Guodong; Fanwick, Philip E.
  • Inorganic Chemistry, Vol. 48, Issue 23
  • DOI: 10.1021/ic901794h

Asymmetric Sulfimidation with cis -β Ru(salalen)(CO) 2 Complexes as Catalyst
journal, September 2007

  • Fujita, Hidekazu; Uchida, Tatsuya; Irie, Ryo
  • Chemistry Letters, Vol. 36, Issue 9
  • DOI: 10.1246/cl.2007.1092

Unsymmetrical salen-type ligands: high yield synthesis of salen-type Schiff bases containing two different benzaldehyde moieties
journal, February 2001


Studies on the oxidation of CuII complexes of quadridentate Schiff bases derived from salicylaldehyde or ortho-aminophenol
journal, September 1996


Unusual Cu(III)—Schiff's base complexes
journal, April 1985


Spectroscopic characterisation of electrogenerated nickel(III) species. Complexes with N2O2 Schiff-base ligands derived from salicylaldehyde
journal, January 1998

  • Freire, Cristina; Castro, Baltazar de
  • Journal of the Chemical Society, Dalton Transactions, Issue 9
  • DOI: 10.1039/a708231b

Theoretical x-ray absorption fine structure standards
journal, July 1991

  • Rehr, J. J.; Mustre de Leon, J.; Zabinsky, S. I.
  • Journal of the American Chemical Society, Vol. 113, Issue 14
  • DOI: 10.1021/ja00014a001

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994

  • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
  • The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
  • DOI: 10.1021/j100096a001

Geometry optimization of molecular structures in solution by the polarizable continuum model
journal, March 1998


The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level
journal, May 1999


A new definition of cavities for the computation of solvation free energies by the polarizable continuum model
journal, August 1997

  • Barone, Vincenzo; Cossi, Maurizio; Tomasi, Jacopo
  • The Journal of Chemical Physics, Vol. 107, Issue 8
  • DOI: 10.1063/1.474671

Influence of Electron-Withdrawing Substituents on the Electronic Structure of Oxidized Ni and Cu Salen Complexes
journal, May 2015


Fully optimized contracted Gaussian basis sets for atoms Li to Kr
journal, August 1992

  • Schäfer, Ansgar; Horn, Hans; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 97, Issue 4
  • DOI: 10.1063/1.463096

Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr
journal, April 1994

  • Schäfer, Ansgar; Huber, Christian; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 100, Issue 8
  • DOI: 10.1063/1.467146

Chemical Redox Agents for Organometallic Chemistry
journal, January 1996

  • Connelly, Neil G.; Geiger, William E.
  • Chemical Reviews, Vol. 96, Issue 2
  • DOI: 10.1021/cr940053x

A Systematic K-edge X-ray Absorption Spectroscopic Study of Cu(III) Sites
journal, June 2000

  • DuBois, Jennifer L.; Mukherjee, Pulakesh; Stack, T. D. P.
  • Journal of the American Chemical Society, Vol. 122, Issue 24
  • DOI: 10.1021/ja993134p

X-ray absorption edge determination of the oxidation state and coordination number of copper. Application to the type 3 site in Rhus vernicifera laccase and its reaction with oxygen
journal, October 1987

  • Kau, Lung Shan; Spira-Solomon, Darlene J.; Penner-Hahn, James E.
  • Journal of the American Chemical Society, Vol. 109, Issue 21
  • DOI: 10.1021/ja00255a032

A Multiplet Analysis of Fe K-Edge 1s → 3d Pre-Edge Features of Iron Complexes
journal, July 1997

  • Westre, Tami E.; Kennepohl, Pierre; DeWitt, Jane G.
  • Journal of the American Chemical Society, Vol. 119, Issue 27
  • DOI: 10.1021/ja964352a

Phenoxyl-copper(II) complexes: models for the active site of galactose oxidase
journal, August 1997

  • Sokolowski, Achim; Leutbecher, Heiko; Weyhermüller, Thomas
  • JBIC Journal of Biological Inorganic Chemistry, Vol. 2, Issue 4
  • DOI: 10.1007/s007750050155

Phenoxyl Radical Complexes of Zinc(II)
journal, September 1997

  • Sokolowski, Achim; Müller, Jochen; Weyhermüller, Thomas
  • Journal of the American Chemical Society, Vol. 119, Issue 38
  • DOI: 10.1021/ja970417d

Ultraviolet Resonance Raman Spectroscopy and General Valence Force Field Analysis of Phenolate and Phenoxyl Radical
journal, April 1995

  • Mukherjee, Arka; McGlashen, Michael L.; Spiro, Thomas G.
  • The Journal of Physical Chemistry, Vol. 99, Issue 14
  • DOI: 10.1021/j100014a007

Resonance Raman Spectroscopic Study of Phenoxyl Radical Complexes
journal, March 1998

  • Schnepf, Robert; Sokolowski, Achim; Müller, Jochen
  • Journal of the American Chemical Society, Vol. 120, Issue 10
  • DOI: 10.1021/ja972269x

Why Does the Active Form of Galactose Oxidase Possess a Diamagnetic Ground State?
journal, March 1998


Aerobic Oxidation of Primary Alcohols (Including Methanol) by Copper(II)− and Zinc(II)−Phenoxyl Radical Catalysts
journal, October 1999

  • Chaudhuri, Phalguni; Hess, Martina; Müller, Jochen
  • Journal of the American Chemical Society, Vol. 121, Issue 41
  • DOI: 10.1021/ja991481t

Oxidation of Benzyl Alcohol with CuII and ZnII Complexes of the Phenoxyl Radical as a Model of the Reaction of Galactose Oxidase
journal, September 1999


Hydrogen atom abstraction by Cu(II)- and Zn(II)-phenoxyl radical complexes, models for the active form of galactose oxidase
journal, January 2000


Mechanistic Insights from Reactions between Copper(II)−Phenoxyl Complexes and Substrates with Activated C−H Bonds
journal, February 2005

  • Pratt, Russell C.; Stack, T. Daniel P.
  • Inorganic Chemistry, Vol. 44, Issue 7
  • DOI: 10.1021/ic048695i

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journal, January 2020

  • Sampani, Stavroula I.; Zdorichenko, Victor; Danopoulou, Marianna
  • Dalton Transactions, Vol. 49, Issue 2
  • DOI: 10.1039/c9dt04146j

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journal, May 2020

  • Paul, Melanie; Teubner, Melissa; Grimm‐Lebsanft, Benjamin
  • Chemistry – A European Journal, Vol. 26, Issue 34
  • DOI: 10.1002/chem.202000664

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text, January 2020


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text, January 2020

  • Paul, Melanie; Teubner, Melissa; Grimm‐Lebsanft, Benjamin
  • Deutsches Elektronen-Synchrotron, DESY, Hamburg
  • DOI: 10.3204/pubdb-2020-05091