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

Chiang, Linus; Wasinger, Erik C.; Shimazaki, Yuichi; Young, Jr., Victor; Storr, Tim; Stack, T. Daniel P.

doi:10.1016/j.ica.2017.09.042

Electronic structure and reactivity studies of a nonsymmetric one-electron oxidized Cu^II bis-phenoxide complex

Journal Article · Mon Sep 18 00:00:00 EDT 2017 · Inorganica Chimica Acta

DOI:https://doi.org/10.1016/j.ica.2017.09.042· OSTI ID:1469090

Chiang, Linus ^[1]; Wasinger, Erik C. ^[2]; Shimazaki, Yuichi ^[3]; Young, Jr., Victor ^[4]; Storr, Tim ^[5]; Stack, T. Daniel P. ^[6]

Stanford Univ., Stanford, CA (United States); Univ. of the Fraser Valley, Abbotsford, BC (Canada)
California State Univ., Chico, CA (United States)
Ibaraki Univ., Mito (Japan)
The Univ. of Minnesota, Minneapolis, MN (United States)
Simon Fraser Univ., Burnaby, BC (Canada)
Stanford Univ., Stanford, CA (United States)

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 Cu^II, 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 Cu^II-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) Cu^II-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 Cu^II, 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 Cu^II-salen analogue, and does not exhibit a substrate-binding pre-equilibrium as observed for the oxidized bis-aminophenoxide Cu^II-salan derivative.

View Accepted Manuscript (DOE)

Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-76SF00515

OSTI ID:: 1469090

Alternate ID(s):: OSTI ID: 1702083

Journal Information:: Inorganica Chimica Acta, Journal Name: Inorganica Chimica Acta Journal Issue: C Vol. 481; ISSN 0020-1693

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (90)

Geometry optimization of molecular structures in solution by the polarizable continuum model Barone, Vincenzo; Cossi, Maurizio; Tomasi, Jacopo Journal of Computational Chemistry, Vol. 19, Issue 4 https://doi.org/10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W	journal	March 1998
Why Does the Active Form of Galactose Oxidase Possess a Diamagnetic Ground State? Müller, Jochen; Weyhermüller, Thomas; Bill, Eckhard Angewandte Chemie International Edition, Vol. 37, Issue 5 https://doi.org/10.1002/(SICI)1521-3773(19980316)37:5<616::AID-ANIE616>3.0.CO;2-4	journal	March 1998
Oxidation of Benzyl Alcohol with CuII and ZnII Complexes of the Phenoxyl Radical as a Model of the Reaction of Galactose Oxidase Itoh, Shinobu; Taki, Masayasu; Takayama, Shigehisa Angewandte Chemie International Edition, Vol. 38, Issue 18 https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18<2774::AID-ANIE2774>3.0.CO;2-E	journal	September 1999
A Structural and Functional Model of Galactose Oxidase: Control of the One-Electron Oxidized Active Form through Two Differentiated Phenolic Arms in a Tripodal Ligand Thomas, Fabrice; Gellon, GisÃ¨le; Gautier-Luneau, Isabelle Angewandte Chemie International Edition, Vol. 41, Issue 16 https://doi.org/10.1002/1521-3773(20020816)41:16<3047::AID-ANIE3047>3.0.CO;2-W	journal	August 2002
A Practical and Versatile Access to Dihydrosalen (Salalen) Ligands: Highly Enantioselective TitaniumIn Situ Catalysts for Asymmetric Epoxidation with Aqueous Hydrogen Peroxide Berkessel, Albrecht; Brandenburg, Marc; Leitterstorf, Eva Advanced Synthesis & Catalysis, Vol. 349, Issue 14-15 https://doi.org/10.1002/adsc.200700221	journal	October 2007
The Geometric and Electronic Structure of a One-Electron-Oxidized Nickel(II) Bis(salicylidene)diamine Complex Storr, Tim; Wasinger, Erik C.; Pratt, Russell C. Angewandte Chemie International Edition, Vol. 46, Issue 27 https://doi.org/10.1002/anie.200701194	journal	July 2007
X-Ray Structures of Copper(II) and Nickel(II) Radical Salen Complexes: The Preference of Galactose Oxidase for Copper(II) Orio, Maylis; Jarjayes, Olivier; Kanso, Hussein Angewandte Chemie International Edition, Vol. 49, Issue 29 https://doi.org/10.1002/anie.201001040	journal	April 2010
Redox-Active Ligands in Catalysis Praneeth, Vijayendran K. K.; Ringenberg, Mark R.; Ward, Thomas R. Angewandte Chemie International Edition, Vol. 51, Issue 41 https://doi.org/10.1002/anie.201204100	journal	September 2012
Titanium cis -1,2-Diaminocyclohexane Salalen Catalysts of Outstanding Activity and Enantioselectivity for the Asymmetric Epoxidation of Nonconjugated Terminal Olefins with Hydrogen Peroxide Lansing, Markus; Engler, Hauke; Leuther, Tobias M. ChemCatChem, Vol. 8, Issue 24 https://doi.org/10.1002/cctc.201601154	journal	December 2016
Fine Tuning of the Oxidation Locus, and Electron Transfer, in Nickel Complexes of Pro-Radical Ligands Rotthaus, Olaf; Jarjayes, Olivier; Thomas, Fabrice Chemistry - A European Journal, Vol. 12, Issue 8 https://doi.org/10.1002/chem.200500915	journal	March 2006
Valence Tautomerism in Octahedral and Square-Planar Phenoxyl–Nickel(II) Complexes: Are Imino Nitrogen Atoms Good Friends? Rotthaus, Olaf; Thomas, Fabrice; Jarjayes, Olivier Chemistry - A European Journal, Vol. 12, Issue 26 https://doi.org/10.1002/chem.200600258	journal	September 2006
Ligand Radical Localization in a Nonsymmetric One-Electron Oxidized NiII Bis-phenoxide Complex Storr, Tim; Verma, Pratik; Shimazaki, Yuichi Chemistry - A European Journal, Vol. 16, Issue 30 https://doi.org/10.1002/chem.201001401	journal	July 2010
One-Electron Oxidized Copper(II) Salophen Complexes: Phenoxyl versus Diiminobenzene Radical Species Kochem, Amélie; Jarjayes, Olivier; Baptiste, Benoit Chemistry - A European Journal, Vol. 18, Issue 4 https://doi.org/10.1002/chem.201102882	journal	December 2011
Radical Localization in a Series of Symmetric Ni ^II Complexes with Oxidized Salen Ligands Chiang, Linus; Kochem, Amélie; Jarjayes, Olivier Chemistry - A European Journal, Vol. 18, Issue 44 https://doi.org/10.1002/chem.201201410	journal	September 2012
Class III Delocalization and Exciton Coupling in a Bimetallic Bis-ligand Radical Complex Dunn, Tim J.; Chiang, Linus; Ramogida, Caterina F. Chemistry - A European Journal, Vol. 19, Issue 29 https://doi.org/10.1002/chem.201300798	journal	June 2013
A Square-Planar Nickel(II) Monoradical Complex with a Bis(salicylidene)diamine Ligand Benisvy, Laurent; Kannappan, Ramu; Song, Yu-Fei European Journal of Inorganic Chemistry, Vol. 2007, Issue 5 https://doi.org/10.1002/ejic.200601015	journal	February 2007
Ten Years of a Biomimetic Approach to the Copper(II) Radical Site of Galactose Oxidase Thomas, Fabrice European Journal of Inorganic Chemistry, Vol. 2007, Issue 17 https://doi.org/10.1002/ejic.200601091	journal	May 2007
The Shrinking World of Innocent Ligands: Conventionaland Non-Conventional Redox-Active Ligands Kaim, Wolfgang European Journal of Inorganic Chemistry, Vol. 2012, Issue 3 https://doi.org/10.1002/ejic.201101359	journal	January 2012
Detailed Geometric and Electronic Structures of a One-Electron-Oxidized Ni Salophen Complex and Its Amido Derivatives: One-Electron-Oxidized Ni Salophen Complex Lecarme, Laureline; Chiang, Linus; Philouze, Christian European Journal of Inorganic Chemistry, Vol. 2014, Issue 22 https://doi.org/10.1002/ejic.201402265	journal	June 2014
Phenoxyl-copper(II) complexes: models for the active site of galactose oxidase Sokolowski, Achim; Leutbecher, Heiko; Weyhermüller, Thomas JBIC Journal of Biological Inorganic Chemistry, Vol. 2, Issue 4 https://doi.org/10.1007/s007750050155	journal	August 1997
Studies on the oxidation of CuII complexes of quadridentate Schiff bases derived from salicylaldehyde or ortho-aminophenol Pasini, Alessandro; Bernini, Elisa; Scaglia, Mauro Polyhedron, Vol. 15, Issue 24 https://doi.org/10.1016/0277-5387(96)00195-7	journal	September 1996
Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects Miertuš, S.; Scrocco, E.; Tomasi, J. Chemical Physics, Vol. 55, Issue 1 https://doi.org/10.1016/0301-0104(81)85090-2	journal	February 1981
Unusual Cu(III)—Schiff's base complexes Abu-El-Wafa, S. M.; Issa, R. M.; McAuliffe, C. A. Inorganica Chimica Acta, Vol. 99, Issue 1 https://doi.org/10.1016/S0020-1693(00)86056-9	journal	April 1985
Resonance Raman evidence for tyrosine involvement in the radical site of galactose oxidase Whittaker, M. M.; DeVito, V. L.; Asher, S. A. Journal of Biological Chemistry, Vol. 264, Issue 13 https://doi.org/10.1016/S0021-9258(18)83205-7	journal	May 1989
A tyrosine-derived free radical in apogalactose oxidase. Whittaker, M. M.; Whittaker, J. W. Journal of Biological Chemistry, Vol. 265, Issue 17 https://doi.org/10.1016/S0021-9258(19)38711-3	journal	June 1990
Unsymmetrical salen-type ligands: high yield synthesis of salen-type Schiff bases containing two different benzaldehyde moieties Campbell, E. Joseph; Nguyen, SonBinh T. Tetrahedron Letters, Vol. 42, Issue 7 https://doi.org/10.1016/S0040-4039(00)02226-7	journal	February 2001
Catalytic asymmetric epoxidation of unfunctionalized olefins Irie, Ryo; Noda, Keiko; Ito, Yoshio Tetrahedron Letters, Vol. 31, Issue 50 https://doi.org/10.1016/S0040-4039(00)88562-7	journal	January 1990
Mixed Valence Chemistry-A Survey and Classification Robin, Melvin B.; Day, Peter Advances in Inorganic Chemistry and Radiochemistry https://doi.org/10.1016/S0065-2792(08)60179-X	book	January 1968
Hydrogen atom abstraction by Cu(II)- and Zn(II)-phenoxyl radical complexes, models for the active form of galactose oxidase Taki, Masayasu; Kumei, Hideyuki; Itoh*, Shinobu Journal of Inorganic Biochemistry, Vol. 78, Issue 1 https://doi.org/10.1016/S0162-0134(99)00198-1	journal	January 2000
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 Tomasi, J.; Mennucci, B.; Cancès, E. Journal of Molecular Structure: THEOCHEM, Vol. 464, Issue 1-3 https://doi.org/10.1016/S0166-1280(98)00553-3	journal	May 1999
Copper-tyrosyl radical enzymes Rogers, M. Current Opinion in Chemical Biology, Vol. 7, Issue 2 https://doi.org/10.1016/S1367-5931(03)00024-3	journal	April 2003
Recent advances in phenoxyl radical complexes of salen-type ligands as mixed-valent galactose oxidase models Lyons, Christopher T.; Stack, T. Daniel P. Coordination Chemistry Reviews, Vol. 257, Issue 2 https://doi.org/10.1016/j.ccr.2012.06.003	journal	January 2013
Effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward asymmetric nitroaldol reactions Kannan, Masanam; Punniyamurthy, Tharmalingam Tetrahedron: Asymmetry, Vol. 25, Issue 18-19 https://doi.org/10.1016/j.tetasy.2014.07.013	journal	October 2014
Influence of Electron-Withdrawing Substituents on the Electronic Structure of Oxidized Ni and Cu Salen Complexes Chiang, Linus; Herasymchuk, Khrystyna; Thomas, Fabrice Inorganic Chemistry, Vol. 54, Issue 12 https://doi.org/10.1021/acs.inorgchem.5b00783	journal	May 2015
Redox Noninnocence of the Bridge in Copper(II) Salophen and Bis(oxamato) Complexes de Bellefeuille, David; Orio, Maylis; Barra, Anne-Laure Inorganic Chemistry, Vol. 54, Issue 18 https://doi.org/10.1021/acs.inorgchem.5b01285	journal	September 2015
Isoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes Talsi, Evgenii P.; Rybalova, Tatyana V.; Bryliakov, Konstantin P. ACS Catalysis, Vol. 5, Issue 8 https://doi.org/10.1021/acscatal.5b01212	journal	July 2015
Free Radical Catalysis by Galactose Oxidase Whittaker, James W. Chemical Reviews, Vol. 103, Issue 6 https://doi.org/10.1021/cr020425z	journal	June 2003
Chromium− and Manganese−salen Promoted Epoxidation of Alkenes McGarrigle, Eoghan M.; Gilheany, Declan G. Chemical Reviews, Vol. 105, Issue 5 https://doi.org/10.1021/cr0306945	journal	May 2005
Making Plastics from Carbon Dioxide: Salen Metal Complexes as Catalysts for the Production of Polycarbonates from Epoxides and CO ₂ Darensbourg, Donald J. Chemical Reviews, Vol. 107, Issue 6 https://doi.org/10.1021/cr068363q	journal	June 2007
Chemical Redox Agents for Organometallic Chemistry Connelly, Neil G.; Geiger, William E. Chemical Reviews, Vol. 96, Issue 2 https://doi.org/10.1021/cr940053x	journal	January 1996
Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions Lyaskovskyy, Volodymyr; de Bruin, Bas ACS Catalysis, Vol. 2, Issue 2 https://doi.org/10.1021/cs200660v	journal	January 2012
Comparative study on the coordination chemistry of cobalt(II), nickel(II), and copper(II) with derivatives of salen and tetrahydrosalen: metal-catalyzed oxidative dehydrogenation of the carbon-nitrogen bond in coordinated tetrahydrosalen Boettcher, Arnd; Elias, Horst; Jaeger, Ernst Gottfried Inorganic Chemistry, Vol. 32, Issue 19 https://doi.org/10.1021/ic00071a028	journal	September 1993
Mechanistic Insights from Reactions between Copper(II)−Phenoxyl Complexes and Substrates with Activated C−H Bonds Pratt, Russell C.; Stack, T. Daniel P. Inorganic Chemistry, Vol. 44, Issue 7 https://doi.org/10.1021/ic048695i	journal	February 2005
Preface: Forum on Redox-Active Ligands Chirik, Paul J. Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic201881k	journal	October 2011
Ligand Contributions to the Electronic Structures of the Oxidized Cobalt(II) salen Complexes Kochem, Amélie; Kanso, Hussein; Baptiste, Benoit Inorganic Chemistry, Vol. 51, Issue 20 https://doi.org/10.1021/ic300763t	journal	September 2012
Reversible Double Oxidation and Protonation of the Non-Innocent Bridge in a Nickel(II) Salophen Complex de Bellefeuille, David; Askari, Mohammad S.; Lassalle-Kaiser, Benedikt Inorganic Chemistry, Vol. 51, Issue 23 https://doi.org/10.1021/ic301684h	journal	November 2012
New Insights into the Electronic Structure and Reactivity of One-Electron Oxidized Copper(II)-(Disalicylidene)diamine Complexes Asami, Kazutaka; Tsukidate, Kazuaki; Iwatsuki, Satoshi Inorganic Chemistry, Vol. 51, Issue 22 https://doi.org/10.1021/ic3018503	journal	October 2012
Unique Ligand-Radical Character of an Activated Cobalt Salen Catalyst That Is Generated by Aerobic Oxidation of a Cobalt(II) Salen Complex Kurahashi, Takuya; Fujii, Hiroshi Inorganic Chemistry, Vol. 52, Issue 7 https://doi.org/10.1021/ic302677f	journal	June 2012
Detailed Evaluation of the Geometric and Electronic Structures of One-Electron Oxidized Group 10 (Ni, Pd, and Pt) Metal(II)-(Disalicylidene)diamine Complexes Shimazaki, Yuichi; Stack, T. Daniel P.; Storr, Tim Inorganic Chemistry, Vol. 48, Issue 17 https://doi.org/10.1021/ic901003q	journal	September 2009
An Efficient Method for the Preparation of Oxo Molybdenum Salalen Complexes and Their Unusual Use as Hydrosilylation Catalysts Ziegler, Jeanette E.; Du, Guodong; Fanwick, Philip E. Inorganic Chemistry, Vol. 48, Issue 23 https://doi.org/10.1021/ic901794h	journal	October 2009
Spin Interaction in Octahedral Zinc Complexes of Mono- and Diradical Schiff and Mannich Bases Orio, M.; Philouze, C.; Jarjayes, O. Inorganic Chemistry, Vol. 49, Issue 2 https://doi.org/10.1021/ic901846u	journal	December 2009
Ultraviolet Resonance Raman Spectroscopy and General Valence Force Field Analysis of Phenolate and Phenoxyl Radical Mukherjee, Arka; McGlashen, Michael L.; Spiro, Thomas G. The Journal of Physical Chemistry, Vol. 99, Issue 14 https://doi.org/10.1021/j100014a007	journal	April 1995
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Theoretical x-ray absorption fine structure standards Rehr, J. J.; Mustre de Leon, J.; Zabinsky, S. I. Journal of the American Chemical Society, Vol. 113, Issue 14 https://doi.org/10.1021/ja00014a001	journal	July 1991
Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane Jacobsen, Eric N.; Zhang, Wei; Muci, Alexander R. Journal of the American Chemical Society, Vol. 113, Issue 18 https://doi.org/10.1021/ja00018a068	journal	August 1991
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 Kau, Lung Shan; Spira-Solomon, Darlene J.; Penner-Hahn, James E. Journal of the American Chemical Society, Vol. 109, Issue 21 https://doi.org/10.1021/ja00255a032	journal	October 1987
One-Electron Oxidized Nickel(II)−(Disalicylidene)diamine Complex: Temperature-Dependent Tautomerism between Ni(III)−Phenolate and Ni(II)−Phenoxyl Radical States Shimazaki, Yuichi; Tani, Fumito; Fukui, Kôichi Journal of the American Chemical Society, Vol. 125, Issue 35 https://doi.org/10.1021/ja035806o	journal	August 2003
Intramolecular Charge Transfer and Biomimetic Reaction Kinetics in Galactose Oxidase Model Complexes Pratt, Russell C.; Stack, T. Daniel P. Journal of the American Chemical Society, Vol. 125, Issue 29 https://doi.org/10.1021/ja035837j	journal	July 2003
Syntheses and Electronic Structures of One-Electron-Oxidized Group 10 Metal(II)−(Disalicylidene)diamine Complexes (Metal = Ni, Pd, Pt) Shimazaki, Yuichi; Yajima, Tatsuo; Tani, Fumito Journal of the American Chemical Society, Vol. 129, Issue 9 https://doi.org/10.1021/ja067022r	journal	March 2007
One-Electron Oxidation of Electronically Diverse Manganese(III) and Nickel(II) Salen Complexes: Transition from Localized to Delocalized Mixed-Valence Ligand Radicals Kurahashi, Takuya; Fujii, Hiroshi Journal of the American Chemical Society, Vol. 133, Issue 21 https://doi.org/10.1021/ja2016813	journal	June 2011
Electrochemical and Spectroscopic Effects of Mixed Substituents in Bis(phenolate)–Copper(II) Galactose Oxidase Model Complexes Pratt, Russell C.; Lyons, Christopher T.; Wasinger, Erik C. Journal of the American Chemical Society, Vol. 134, Issue 17 https://doi.org/10.1021/ja211247f	journal	April 2012
Defining the Electronic and Geometric Structure of One-Electron Oxidized Copper−Bis-phenoxide Complexes Storr, Tim; Verma, Pratik; Pratt, Russell C. Journal of the American Chemical Society, Vol. 130, Issue 46 https://doi.org/10.1021/ja804339m	journal	October 2008
A Multiplet Analysis of Fe K-Edge 1s → 3d Pre-Edge Features of Iron Complexes Westre, Tami E.; Kennepohl, Pierre; DeWitt, Jane G. Journal of the American Chemical Society, Vol. 119, Issue 27 https://doi.org/10.1021/ja964352a	journal	July 1997
Phenoxyl Radical Complexes of Zinc(II) Sokolowski, Achim; Müller, Jochen; Weyhermüller, Thomas Journal of the American Chemical Society, Vol. 119, Issue 38 https://doi.org/10.1021/ja970417d	journal	September 1997
Resonance Raman Spectroscopic Study of Phenoxyl Radical Complexes Schnepf, Robert; Sokolowski, Achim; Müller, Jochen Journal of the American Chemical Society, Vol. 120, Issue 10 https://doi.org/10.1021/ja972269x	journal	March 1998
Aerobic Oxidation of Primary Alcohols (Including Methanol) by Copper(II)− and Zinc(II)−Phenoxyl Radical Catalysts Chaudhuri, Phalguni; Hess, Martina; Müller, Jochen Journal of the American Chemical Society, Vol. 121, Issue 41 https://doi.org/10.1021/ja991481t	journal	October 1999
A Systematic K-edge X-ray Absorption Spectroscopic Study of Cu(III) Sites DuBois, Jennifer L.; Mukherjee, Pulakesh; Stack, T. D. P. Journal of the American Chemical Society, Vol. 122, Issue 24 https://doi.org/10.1021/ja993134p	journal	June 2000
Alternating Copolymerization of Cyclohexene Oxide with Carbon Dioxide Catalyzed by (salalen)CrCl Complexes Nakano, Koji; Nakamura, Mitsuru; Nozaki, Kyoko Macromolecules, Vol. 42, Issue 18 https://doi.org/10.1021/ma9012626	journal	September 2009
Biologically inspired oxidation catalysis Que, Lawrence; Tolman, William B. Nature, Vol. 455, Issue 7211 https://doi.org/10.1038/nature07371	journal	September 2008
Metal–Salen Schiff base complexes in catalysis: practical aspects Cozzi, Pier Giorgio Chem. Soc. Rev., Vol. 33, Issue 7 https://doi.org/10.1039/B307853C	journal	January 2004
Redox-active ligands in catalysis Luca, Oana R.; Crabtree, Robert H. Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35228A	journal	January 2013
Spectroscopic characterisation of electrogenerated nickel(III) species. Complexes with N2O2 Schiff-base ligands derived from salicylaldehyde Freire, Cristina; Castro, Baltazar de Journal of the Chemical Society, Dalton Transactions, Issue 9 https://doi.org/10.1039/a708231b	journal	January 1998
A functional model of galactose oxidase: catalytic oxidation of primary alcohols with a one-electron oxidized copper(II) complex Saint-Aman, Eric; Me´nage, Ste´phane; Pierre, Jean-Louis New Journal of Chemistry, Vol. 22, Issue 5 https://doi.org/10.1039/a801588k	journal	January 1998
Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis Canali, Laetitia; Sherrington, David C. Chemical Society Reviews, Vol. 28, Issue 2 https://doi.org/10.1039/a806483k	journal	January 1999
Up to four phenoxyl radicals coordinated to two metal ions in copper and zinc complexes? Rotthaus, Olaf; Jarjayes, Olivier; Thomas, Fabrice Dalton Transactions, Issue 8 https://doi.org/10.1039/b612068g	journal	January 2007
A versatile electronic hole in one-electron oxidized NiIIbis-salicylidene phenylenediamine complexes Rotthaus, Olaf; Jarjayes, Olivier; Perez Del Valle, Carlos Chemical Communications, Issue 43 https://doi.org/10.1039/b710027b	journal	January 2007
One-electron oxidized nickel(II) complexes of bis and tetra(salicylidene) phenylenediamine Schiff bases: from monoradical to interacting Ni(III) ions Rotthaus, Olaf; Jarjayes, Olivier; Philouze, Christian Dalton Transactions, Issue 10 https://doi.org/10.1039/b811702k	journal	January 2009
Influence of the chelate effect on the electronic structure of one-electron oxidized group 10 metal(ii)-(disalicylidene)diamine complexes Shimazaki, Yuichi; Arai, Natsumi; Dunn, Tim J. Dalton Transactions, Vol. 40, Issue 11 https://doi.org/10.1039/c0dt01574a	journal	January 2011
Double oxidation localizes spin in a Ni bis-phenoxyl radical complex Dunn, Tim J.; Webb, Michael I.; Hazin, Khatera Dalton Transactions, Vol. 42, Issue 11 https://doi.org/10.1039/c2dt32632a	journal	January 2013
The chemistry and applications of multimetallic salen complexes Clarke, Ryan M.; Storr, Tim Dalton Transactions, Vol. 43, Issue 25 https://doi.org/10.1039/c4dt00591k	journal	January 2014
400. The determination of the paramagnetic susceptibility of substances in solution by nuclear magnetic resonance Evans, D. F. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9590002003	journal	January 1959
Fully optimized contracted Gaussian basis sets for atoms Li to Kr Schäfer, Ansgar; Horn, Hans; Ahlrichs, Reinhart The Journal of Chemical Physics, Vol. 97, Issue 4 https://doi.org/10.1063/1.463096	journal	August 1992
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr Schäfer, Ansgar; Huber, Christian; Ahlrichs, Reinhart The Journal of Chemical Physics, Vol. 100, Issue 8 https://doi.org/10.1063/1.467146	journal	April 1994
A new definition of cavities for the computation of solvation free energies by the polarizable continuum model Barone, Vincenzo; Cossi, Maurizio; Tomasi, Jacopo The Journal of Chemical Physics, Vol. 107, Issue 8 https://doi.org/10.1063/1.474671	journal	August 1997
Sulfanyl stabilization of copper-bonded phenoxyls in model complexes and galactose oxidase Verma, P.; Pratt, R. C.; Storr, T. Proceedings of the National Academy of Sciences, Vol. 108, Issue 46 https://doi.org/10.1073/pnas.1109931108	journal	November 2011
Glyoxal Oxidase from Phanerochaete chrysosporium Is a New Radical-Copper Oxidase Whittaker, Mei M.; Kersten, Philip J.; Nakamura, Nobuhumi Journal of Biological Chemistry, Vol. 271, Issue 2 https://doi.org/10.1074/jbc.271.2.681	journal	January 1996
Radical Ligands Confer Nobility on Base-Metal Catalysts Chirik, P. J.; Wieghardt, K. Science, Vol. 327, Issue 5967 https://doi.org/10.1126/science.1183281	journal	February 2010
Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics Rittle, J.; Green, M. T. Science, Vol. 330, Issue 6006 https://doi.org/10.1126/science.1193478	journal	November 2010
Asymmetric Sulfimidation with cis -β Ru(salalen)(CO) ₂ Complexes as Catalyst Fujita, Hidekazu; Uchida, Tatsuya; Irie, Ryo Chemistry Letters, Vol. 36, Issue 9 https://doi.org/10.1246/cl.2007.1092	journal	September 2007

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[Cu ^II {(L ^ISQ )˙ ⁻ } ₂ ] (H ₂ L: thioether-appended o -aminophenol ligand) monocation triggers change in donor site from N ₂ O ₂ to N ₂ O ₍₂₎ S and valence-tautomerism Rajput, Amit; Saha, Anannya; Barman, Suman K. Dalton Transactions, Vol. 48, Issue 5 https://doi.org/10.1039/c8dt03778g	journal	January 2019
Shedding light on the use of Cu( ii )-salen complexes in the A 3 coupling reaction Sampani, Stavroula I.; Zdorichenko, Victor; Danopoulou, Marianna Dalton Transactions, Vol. 49, Issue 2 https://doi.org/10.1039/c9dt04146j	journal	January 2020
Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ-oxo) Copper Complex Paul, Melanie; Teubner, Melissa; Grimm-Lebsanft, Benjamin RWTH Aachen University https://doi.org/10.18154/rwth-2020-05457	text	January 2020
Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis($μ$‐oxo) Copper Complex Paul, Melanie; Teubner, Melissa; Grimm‐Lebsanft, Benjamin Deutsches Elektronen-Synchrotron, DESY, Hamburg https://doi.org/10.3204/pubdb-2020-05091	text	January 2020