Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide

Pella, Bruce J.; Niklas, Jens; Poluektov, Oleg G.; Mukherjee, Anusree

doi:10.1016/j.ica.2018.07.035

Title: Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide

Abstract

Cu(II) complexes bearing N2/Py2 tetradentate ligands consisting of two pyridyl arms and a flexible ethyldiamine backbone, [(BPMEN)Cu(ClO₄)₂] (1), with rigid cyclohexyl backbone [(BPMCN)Cu(ClO₄)₂] (2), and substituted with bispyrrolidyl [(PDP)Cu(ClO₄)₂] (3), and Cu(II) complex bearing N2/Py3 pentadentate ligand, [(TPMEN)Cu(ClO₄)₂] (4), were synthesized and structurally characterized. Reactivity of 1–4 with cumyl hydroperoxide was investigated to study the effects of ligand rigidity and denticity on the mechanism of O–O bond cleavage. Results presented herein illustrate that 1–3 favors homolysis, however 4 showed little to almost no impact on O–O bond cleavage.

Authors:

Pella, Bruce J. ^[1]; Niklas, Jens ^[2]; Poluektov, Oleg G. ^[2]; Mukherjee, Anusree ^[1]

Univ. of Alabama, Huntsville, AL (United States). Dept. of Chemistry
Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Science and Engineering Division

Publication Date:: Tue Jul 24 00:00:00 EDT 2018

Research Org.:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

OSTI Identifier:: 1473686

Alternate Identifier(s):: OSTI ID: 1703179

Grant/Contract Number:: AC02-06CH11357

Resource Type:: Accepted Manuscript

Journal Name:: Inorganica Chimica Acta

Additional Journal Information:: Journal Volume: 483; 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; O-O bond cleavage mechanism; complex characterization; copper coordination chemistry; cumyl hydroperoxide; oxidation reactions

Citation Formats


                    Pella, Bruce J., Niklas, Jens, Poluektov, Oleg G., and Mukherjee, Anusree. Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide.  United States: N. p., 2018. 
Web.  doi:10.1016/j.ica.2018.07.035.

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                    Pella, Bruce J., Niklas, Jens, Poluektov, Oleg G., & Mukherjee, Anusree. Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide.  United States.  https://doi.org/10.1016/j.ica.2018.07.035

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                    Pella, Bruce J., Niklas, Jens, Poluektov, Oleg G., and Mukherjee, Anusree. Tue .  
"Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide".  United States.  https://doi.org/10.1016/j.ica.2018.07.035.  https://www.osti.gov/servlets/purl/1473686.

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@article{osti_1473686,

  title        = {Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide},

  author       = {Pella, Bruce J. and Niklas, Jens and Poluektov, Oleg G. and Mukherjee, Anusree},

  abstractNote = {Cu(II) complexes bearing N2/Py2 tetradentate ligands consisting of two pyridyl arms and a flexible ethyldiamine backbone, [(BPMEN)Cu(ClO4)2] (1), with rigid cyclohexyl backbone [(BPMCN)Cu(ClO4)2] (2), and substituted with bispyrrolidyl [(PDP)Cu(ClO4)2] (3), and Cu(II) complex bearing N2/Py3 pentadentate ligand, [(TPMEN)Cu(ClO4)2] (4), were synthesized and structurally characterized. Reactivity of 1–4 with cumyl hydroperoxide was investigated to study the effects of ligand rigidity and denticity on the mechanism of O–O bond cleavage. Results presented herein illustrate that 1–3 favors homolysis, however 4 showed little to almost no impact on O–O bond cleavage.},

  doi          = {10.1016/j.ica.2018.07.035},

  journal      = {Inorganica Chimica Acta},

  number       = C,

  volume       = 483,

  place        = {United States},

  year         = {Tue Jul 24 00:00:00 EDT 2018},

  month        = {Tue Jul 24 00:00:00 EDT 2018}

}

Copy to clipboard

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Title: Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide

Abstract

Citation Formats

Structure and Spectroscopy of Copper−Dioxygen Complexes journal, February 2004

Reactivity of Dioxygen−Copper Systems journal, February 2004

Mechanisms Whereby Mononuclear Copper Proteins Functionalize Organic Substrates journal, January 1996

Amidation of Bioactive Peptides: The Structure of Peptidylglycine -Hydroxylating Monooxygenase journal, November 1997

The Copper-Enzyme Family of Dopamine β-Monooxygenase and Peptidylglycine α-Hydroxylating Monooxygenase: Resolving the Chemical Pathway for Substrate Hydroxylation journal, November 2005

Synthesis, molecular structure, and reactivity of (alkylperoxo)copper(II) complex journal, August 1993

Reactivity of copper(ii)-alkylperoxo complexes journal, January 2011

Heterolytic Alkyl Hydroperoxide O-O Bond Cleavage by Copper(I) Complexes journal, August 2012

Nucleophilic reactivity of copper( ii )–alkylperoxo complexes journal, January 2017

Reactivity of Mononuclear Alkylperoxo Copper(II) Complex. O−O Bond Cleavage and C−H Bond Activation journal, April 2008

Spectroscopic and Theoretical Studies of Mononuclear Copper(II) Alkyl- and Hydroperoxo Complexes: Electronic Structure Contributions to Reactivity journal, October 2000

Geometric effects on O O bond scission of copper(II)-alkylperoxide complexes journal, December 2017

EasySpin, a comprehensive software package for spectral simulation and analysis in EPR journal, January 2006

Mononuclear nickel (II) and copper (II) coordination complexes supported by bispicen ligand derivatives: Experimental and computational studies journal, January 2017

Determining the Fate of a Non-Heme Iron Oxidation Catalyst Under Illumination, Oxygen, and Acid journal, October 2016

A Predictably Selective Aliphatic C H Oxidation Reaction for Complex Molecule Synthesis journal, November 2007

Pentadentate Copper Halide Complexes Have Higher Catalytic Activity in Atom Transfer Radical Polymerization of Methyl Acrylate Than Hexadentate Complexes journal, May 2009

SHELXT – Integrated space-group and crystal-structure determination journal, January 2015

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Synthesis, characterization, and reactivity of copper complexes supported by the TPMEN ligand framework journal, January 2018

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Synthesis, structure, and catalytic activity of chiral Cu(II) and Ag(I) complexes with (S,S)-1,2-diaminocyclohexane-based N4-donor ligands journal, April 2008

Studies on the metalamide bond. II. The crystal structure of the deprotonated copper(II) complex of N,N′-bis-(2′-pyridinecarboxamide)-1,2-benzene journal, January 1980

New Cu(II) complexes with polydentate chelating Schiff base ligands: Synthesis, structures, characterisations and biochemical activity studies journal, January 2007

Synthesis and structural characterization of copper complexes of N4 tetradentate Schiff bases derived from N-alkylated 2-aminobenzaldehyde. Effects of cyclization, oxidation, and dinucleation journal, September 2001

Binuclear Copper(II) Complexes of Bis(pentadentate) Ligands Derived from Alkyl-Bridged Bis(1,4,7-triazacyclonane) Macrocycles journal, January 1996

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Reactivity of Dioxygen−Copper Systems
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Mechanisms Whereby Mononuclear Copper Proteins Functionalize Organic Substrates
journal, January 1996

Amidation of Bioactive Peptides: The Structure of Peptidylglycine -Hydroxylating Monooxygenase
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The Copper-Enzyme Family of Dopamine β-Monooxygenase and Peptidylglycine α-Hydroxylating Monooxygenase: Resolving the Chemical Pathway for Substrate Hydroxylation
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Synthesis, molecular structure, and reactivity of (alkylperoxo)copper(II) complex
journal, August 1993

Reactivity of copper(ii)-alkylperoxo complexes
journal, January 2011

Heterolytic Alkyl Hydroperoxide O-O Bond Cleavage by Copper(I) Complexes
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Nucleophilic reactivity of copper( ii )–alkylperoxo complexes
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Geometric effects on O O bond scission of copper(II)-alkylperoxide complexes
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EasySpin, a comprehensive software package for spectral simulation and analysis in EPR
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Mononuclear nickel (II) and copper (II) coordination complexes supported by bispicen ligand derivatives: Experimental and computational studies
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New Cu(II) complexes with polydentate chelating Schiff base ligands: Synthesis, structures, characterisations and biochemical activity studies
journal, January 2007

Synthesis and structural characterization of copper complexes of N4 tetradentate Schiff bases derived from N-alkylated 2-aminobenzaldehyde. Effects of cyclization, oxidation, and dinucleation
journal, September 2001

Binuclear Copper(II) Complexes of Bis(pentadentate) Ligands Derived from Alkyl-Bridged Bis(1,4,7-triazacyclonane) Macrocycles
journal, January 1996

Five-coordinate metal(II) complexes based pyrazolyl ligands
journal, April 2015

The pentadentate ligands 2PyN2Q and N4Py, and their Cu(II) and Zn(II) complexes: A synthetic, spectroscopic and crystallographic structural study
journal, February 2015

Syntheses, structures and some electrochemistry of Cu(II) complexes with tris[(2-pyridyl)methyl]amine: [Cu{N(CH2-py)3}(N3)]ClO4 (I), [Cu{N(CH2-py)3}(O–NO)]ClO4 (II) and [Cu{N(CH2-py)3}(NCS)]ClO4 (III)
journal, September 2004

Synthesis, Structure and Properties of Five-Coordinate Copper(II) Complexes of Pentadentate Ligands with Pyridyl Pendant Arms
journal, January 1995

The correlation of the electronic properties and stereochemistry of mononuclear {CuN _4–6 } chromophores
journal, January 1972

Unusual EPR Spectra with Inverse Axial g values of Chlorosalicylate–Cu(II)–2,6-Pyridinedimethanol Complex in Frozen Water–Methanol Solution
journal, January 2013