ArticleThe journal of physical chemistry. A2012
Effect of basic site substituents on concerted proton-electron transfer in hydrogen-bonded pyridyl-phenols.
Article in The journal of physical chemistry. A, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 38 citations in OpenAlex.
- Driving Forces and Spin-Gated Reactivity of N5-Hydropyrimidopteridinetetraone Radicals in Photocatalysis.The Journal of organic chemistry · 2026Article
- Multisite Proton-Coupled Electron Transfer at a Keggin-Type Polyoxotungstate.Journal of the American Chemical Society · 2026Article
- Role of Propionate Side Chain in Heme-Containing Metalloenzymes.ACS organic & inorganic Au · 2025Review
- Iridium Polypyridyl Carboxylates as Excited-State PCET Catalysts for the Functionalization of Unactivated C-H Bonds.Journal of the American Chemical Society · 2025Article
- When a Twist Makes a Difference: Exploring PCET and ESIPT on a Nonplanar Hydrogen-Bonded Donor-Acceptor System.The journal of physical chemistry letters · 2024Article
- An Investigation of the Influence of Tyrosine Local Interactions on Electron Hopping in a Model Protein.Molecules (Basel, Switzerland) · 2024Article
- Roles of High-valent Hemes and pH Dependence in Halite Decomposition Catalyzed by Chlorite Dismutase fromACS catalysis · 2022Article
- Structural and Thermodynamic Effects on the Kinetics of C-H Oxidation by Multisite Proton-Coupled Electron Transfer in Fluorenyl Benzoates.The Journal of organic chemistry · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- C-H oxidation in fluorenyl benzoates does not proceed through a stepwise pathway: revisiting asynchronous proton-coupled electron transfer.Chemical science · 2021Article
- Understanding Chemoselectivity in Proton-Coupled Electron Transfer: A Kinetic Study of Amide and Thiol Activation.Journal of the American Chemical Society · 2019Article
- Transition State Asymmetry in C-H Bond Cleavage by Proton-Coupled Electron Transfer.Journal of the American Chemical Society · 2019Article
- Concerted proton-electron transfer reactions in the Marcus inverted region.Science (New York, N.Y.) · 2019Article
- Rate-Driving Force Relationships in the Multisite Proton-Coupled Electron Transfer Activation of Ketones.Journal of the American Chemical Society · 2019Article
- A Continuum of Proton-Coupled Electron Transfer Reactivity.Accounts of chemical research · 2018Article
- Accelerating proton-coupled electron transfer of metal hydrides in catalyst model reactions.Nature chemistry · 2018Article
- Activationless Multiple-Site Concerted Proton-Electron Tunneling.Journal of the American Chemical Society · 2018Article
- Separating Proton and Electron Transfer Effects in Three-Component Concerted Proton-Coupled Electron Transfer Reactions.Journal of the American Chemical Society · 2017Article
- Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities.Topics in current chemistry (Cham) · 2016Review
- Conformational Change with Steric Interactions Affects the Inner Sphere Component of Concerted Proton-Electron Transfer in a Pyridyl-Appended Radical Cation System.The Journal of organic chemistry · 2015Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Separated concerted proton-electron transfer (sCPET) reactions of two series of phenols with pendent substituted pyridyl moieties are described. The pyridine is either attached directly to the phenol (HOAr-pyX) or connected through a methylene linker (HOArCH(2)pyX) (X = 4-NO(2), 5-CF(3), 4-CH(3), and 4-NMe(2)). Electron-donating and -withdrawing substituents have a substantial effect on the chemical environment of the transferring proton, as indicated by IR and (1)H NMR spectra, X-ray structures, and computational studies. One-electron oxidation of the phenols occurs concomitantly with proton transfer from the phenolic oxygen to the pyridyl nitrogen. The oxidation potentials vary linearly with the pK(a) of the free pyridine (pyX), with slopes slightly below the Nerstian value of 59 mV/pK(a). For the HOArCH(2)pyX series, the rate constants k(sCPET) for oxidation by NAr(3)(•+) or [Fe(diimine)(3)](3+) vary primarily with the thermodynamic driving force (ΔG°(sCPET)), whether ΔG° is changed by varying the potential of the oxidant or the substituent on the pyridine, indicating a constant intrinsic barrier λ. In contrast, the substituents in the HOAr-pyX series affect λ as well as ΔG°(sCPET), and compounds with electron-withdrawing substituents have significantly lower reactivity. The relationship between the structural and spectroscopic properties of the phenols and their CPET reactivity is discussed.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.