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Record W1982280780 · doi:10.1021/om900679w

A Kinetics Study of the Oxidative Addition of Bromobenzene to Pd(PCy<sub>3</sub>)<sub>2</sub>(Cy = cyclohexyl) in a Nonpolar Medium: The Influence on Rates of Added PCy<sub>3</sub>and Bromide Ion

2009· article· en· W1982280780 on OpenAlex
Emily A. Mitchell, Philip G. Jessop, Michael C. Baird

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueOrganometallics · 2009
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsQueen's University
Fundersnot available
KeywordsChemistryBromobenzenePalladiumOxidative additionMedicinal chemistryBromideKineticsTolueneOxidative phosphorylationSalt (chemistry)Inorganic chemistryCatalysisPhotochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Bromobenzene oxidatively adds to the palladium(0) compound Pd(PCy 3 ) 2 to give cleanly the palladium(II) product trans -PdBr(Ph)(PCy 3 ) 2 . Kinetics studies of this reaction under pseudo-first-order conditions (excess PhBr) as well as in the presence of 1 molar equiv of PCy 3 or of added bromide ion (as the toluene-soluble tetraoctylphosphonium salt) have been carried out. We find that oxidative addition is first-order in palladium and that, in the absence of added PCy 3, the reaction involves both the 2:1 species Pd(PCy 3 ) 2 and the 1:1 species Pd(PCy 3 ). Interestingly, added PCy 3 results in inhibition of oxidative addition both by decreasing the relative amount of the reactive 1:1 compound and by converting much of the palladium(0) to the kinetically less active 3:1 compound Pd(PCy 3 ) 3 . Added bromide ion has essentially no effect on the rate, surprising in view of previous literature reports.

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.

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)0.002
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 score0.090
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.002
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.002
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
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 head0.010
GPT teacher head0.247
Teacher spread0.236 · 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