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Record W3009914712 · doi:10.1021/acscatal.9b05163

Hydroxide-Induced Degradation of Olefin Metathesis Catalysts: A Challenge for Metathesis in Alkaline Media

2020· article· en· W3009914712 on OpenAlexafffund
Alexandre Y. Goudreault, Daniel M. Walden, Daniel L. Nascimento, Adrian Botti, Stephan N. Steinmann, Carine Michel, Deryn E. Fogg

Bibliographic record

VenueACS Catalysis · 2020
Typearticle
Languageen
FieldChemistry
TopicSynthetic Organic Chemistry Methods
Canadian institutionsUniversity of Ottawa
FundersNatural Sciences and Engineering Research Council of CanadaCentre National de la Recherche ScientifiqueUniversity of OttawaÉcole Normale Supérieure
KeywordsCatalysisMetathesisHydroxideChemistrySalt metathesis reactionOlefin metathesisLigand (biochemistry)Olefin fiberDecompositionDerivative (finance)Degradation (telecommunications)Catalytic cyclePhotochemistryCombinatorial chemistryInorganic chemistryOrganic chemistryPolymerization

Abstract

fetched live from OpenAlex

Hydroxide ion is shown to be a potent disruptor of Ru-catalyzed olefin metathesis, in a study of the Hoveyda catalyst HII. Addition of [NnBu4][OH] immediately terminates metathesis via HII, an effect traced to formation of bis(hydroxide) complex HII–OH. The latter was synthesized for direct study. HII–OH initiates very slowly on reaction with olefins, and decomposes in the first cycle of metathesis. Computational analysis reveals rapid bimolecular coupling between HII–OH and its four-coordinate methylidene derivative. Importantly, fully decomposed catalyst also accelerates decomposition of HII–OH. The H-bonding capacity of the hydroxide ligand is proposed as a powerful driving force for degradation.

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)0.001
metaresearch head score (Gemma)0.005
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.021
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.005
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
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 head0.059
GPT teacher head0.285
Teacher spread0.226 · 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.

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

Citations26
Published2020
Admission routes2
Has abstractyes

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