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Record W2884304826 · doi:10.1021/jacs.8b06336

Extremely Fast Hydrogen Atom Transfer between Nitroxides and HOO<b>·</b> Radicals and Implication for Catalytic Coantioxidant Systems

2018· article· en· W2884304826 on OpenAlexafffund
Andrea Baschieri, Luca Valgimigli, Simone Gabbanini, Gino A. DiLabio, Eduardo Romero‐Montalvo, Riccardo Amorati

Bibliographic record

VenueJournal of the American Chemical Society · 2018
Typearticle
Languageen
FieldChemistry
TopicFree Radicals and Antioxidants
Canadian institutionsUniversity of British Columbia, Okanagan CampusUniversity of British Columbia
FundersUniversità di BolognaNatural Sciences and Engineering Research Council of CanadaConsejo Nacional de Ciencia y TecnologíaCanada Foundation for Innovation
KeywordsChemistryRadicalHydrogen atomCatalysisAtom (system on chip)PhotochemistryMedicinal chemistryComputational chemistryGroup (periodic table)Organic chemistry

Abstract

fetched live from OpenAlex

We report a novel coantioxidant system based on TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl radical) that, in biologically relevant model systems, rapidly converts chain-carrying alkylperoxyl radicals to HOO·. Extremely efficient quenching of HOO· by TEMPO blocks the oxidative chain. Rate constants in chlorobenzene were measured to be 1.1 × 109 M–1 s–1 for the reductive reaction TEMPO + HOO· → TEMPOH + O2 and 5.0 × 107 M–1 s–1 for the oxidative reaction TEMPOH + HOO· → TEMPO + H2O2. These rate constants are significantly higher than that associated with the reaction of HOO· with α-tocopherol, Nature’s best lipid soluble antioxidant (k = 1.6 × 106 M–1 s–1). These data show that in the presence of ROO·-to-HOO· chain-transfer agents, which are common in lipophilic environments, the TEMPO/TEMPOH couple protects organic molecules from oxidation by establishing an efficient reductive catalytic cycle. This catalytic cycle provides a new understanding of the efficacy of the antioxidant capability of TEMPO in nonaqueous systems and its potential to act as a chemoprotective against radical damage.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.005
Threshold uncertainty score0.525

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.015
GPT teacher head0.252
Teacher spread0.237 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations50
Published2018
Admission routes2
Has abstractyes

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Same venueJournal of the American Chemical SocietySame topicFree Radicals and AntioxidantsFrench-language works237,207