ArticleJournal of the American Chemical Society2015
Hydrogen atom abstraction from hydrocarbons by a copper(III)-hydroxide complex.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 75 papers.
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Who cites it
75 citing papers in PubMed.
- Copper(II/III) Redox Couple Enables C─H Methylation via a Radical Mechanism Analogous to SAM Enzymes.Angewandte Chemie (International ed. in English) · 2026Article
- Lewis acidity of a high-valent copper(iii) acetylacetonate.RSC advances · 2026Article
- High-Valent Late Transition Metal-Oxo Complexes: Breaking Boundaries at the Oxo Wall and Beyond.Chemical reviews · 2026Review
- Unprecedented Formation of a Formally Cu(III) Trifluoromethyl Hydroxide Tetramer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Distinct hydrogen atom transfer and radical capture reactivity of copper(iii) OH/F complexes enables site-selective C(spChemical science · 2026Article
- Hydrogen Atom Abstraction via Hydride-Coupled Electron Transfer and Its Origin.Inorganic chemistry · 2025Article
- The Role of Electron Transfer in Copper-Mediated C(spAngewandte Chemie (International ed. in English) · 2025Article
- Pinpointing Cu-Coordination Motifs in Bio-Inspired MOFs by Combining DFT-Assisted XAS Analysis and Multivariate Curve Resolution.The journal of physical chemistry. C, Nanomaterials and interfaces · 2025Article
- From [2Mn2S] Diamond Cores to Butterfly Rhombs: Transformations That Highlight Alternating Peptide Binding Sites.Inorganic chemistry · 2024Article
- High pressure-derived nonsymmetrical [CuScience advances · 2024Article
- Fresh Impetus in the Chemistry of Calcium Peroxides.Journal of the American Chemical Society · 2024Article
- Copper-oxygen adducts: new trends in characterization and properties towards C-H activation.Chemical science · 2024Review
- Functional Model of Compound II of Cytochrome P450: Spectroscopic Characterization and Reactivity Studies of a FeJACS Au · 2024Article
- A designed Copper Histidine-brace enzyme for oxidative depolymerization of polysaccharides as a model of lytic polysaccharide monooxygenase.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- A Conserved Second Sphere Residue Tunes Copper Site Reactivity in Lytic Polysaccharide Monooxygenases.Journal of the American Chemical Society · 2023Article
- Lytic polysaccharide monooxygenases: enzymes for controlled and site-specific Fenton-like chemistry.Essays in biochemistry · 2023Article
- Molecular Mechanism of Substrate Oxidation in Lytic Polysaccharide Monooxygenases: Insight from Theoretical Investigations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Review
- C(spChemical science · 2023Article
- Copper-Catalyzed Electrochemical C-H Fluorination.Chem catalysis · 2023Article
- Capture of activated dioxygen intermediates at the copper-active site of a lytic polysaccharide monooxygenase.Chemical science · 2022Article
15 more citing papers are in PubMed but not listed here.
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Authors and funding
2 authors.
Funding
Abstract
With the aim of understanding the basis for the high rate of hydrogen atom abstraction (HAT) from dihydroanthracene (DHA) by the complex LCuOH (1; L = N,N'-bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamide), the bond dissociation enthalpy of the reaction product LCu(H2O) (2) was determined through measurement of its pK(a) and E(1/2) in THF solution. In so doing, an equilibrium between 2 and LCu(THF) was characterized by UV-vis and EPR spectroscopy and cyclic voltammetry (CV). A high pK(a) of 18.8 ± 1.8 and a low E(1/2) of -0.074 V vs Fc/Fc(+) in THF combined to yield an O-H BDE for 2 of 90 ± 3 kcal mol(-1) that is large relative to values for most transition metal oxo/hydroxo complexes. By taking advantage of the increased stability of 1 observed in 1,2-difluorobenzene (DFB) solvent, the kinetics of the reactions of 1 with a range of substrates with varying BDE values for their C-H bonds were measured. The oxidizing power of 1 was revealed through the accelerated decay of 1 in the presence of the substrates, including THF (BDE = 92 kcal mol(-1)) and cyclohexane (BDE = 99 kcal mol(-1)). CV experiments in THF solvent showed that 1 reacted with THF via rate-determining attack at the THF C-H(D) bonds with a kinetic isotope effect of 10.2. Analysis of the kinetic and thermodynamic data provides new insights into the basis for the high reactivity of 1 and the possible involvement of species like 1 in oxidation catalysis.
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