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Record W1994721258 · doi:10.1039/b009494n

Absolute rate constants for some reactions of the triethylamine-boryl radical and the borane radical anion

2001· article· en· W1994721258 on OpenAlex
Brad Sheeller, K. U. Ingold

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

VenueJournal of the Chemical Society Perkin Transactions 2 · 2001
Typearticle
Languageen
FieldPhysics and Astronomy
TopicAdvanced Chemical Physics Studies
Canadian institutionsSteacie Institute for Molecular Sciences
Fundersnot available
KeywordsChemistryReaction rate constantRadicalFlash photolysisPhotochemistryNucleophileHydrogen atom abstractionMedicinal chemistryPeroxideHomolysisTriethylamineKineticsOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Laser flash photolysis (LFP) of di-tert-butyl peroxide or dicumyl peroxide at ambient temperatures in the presence of Et3N→BH3 or BH4− generated the title radicals which were found to have broad, featureless absorptions in the visible region. Rate constants for H-atom abstraction from Et3N→BH3 by cumyloxyl radicals show a small solvent dependence, e.g. 12 × 107 and 2.2 × 107 dm3 mol−1 s−1 in isooctane and acetonitrile, respectively. Rate constants for halogen atom abstraction by Et3N→BH2˙ and BH3˙− from a number of chlorides and bromides were determined by LFP and by competitive kinetics, e.g., for Et3N→BH2˙ + CCl4/PhCH2Cl/CH3(CH2)2Cl, k = 4.4 × 109/1.1 × 107/5.1 × 105 dm3 mol−1 s−1 and for BH3˙− + CCl4/PhCH2Cl, k = 2.0 × 109/3.0 × 107 dm3 mol−1 s−1. Rates of addition of Et3N→BH2˙ to 1- and 1,1-substituted olefins increase dramatically as the electron affinity of the olefin increases, confirming the nucleophilic character of amine-boryl radicals. A comparison of the present results with literature data for the addition of olefins of four nucleophilic carbon-centered radicals proves that Et3N→BH2˙ is by far the most nucleophilic radical for which kinetic data are available. A few rate constants for abstraction of hydrogen from electron-deficient carbon by Et3N→BH2˙ are also reported.

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)0.000
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 score0.249
Threshold uncertainty score0.563

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.001
Bibliometrics0.0000.000
Science and technology studies0.0000.002
Scholarly communication0.0000.000
Open science0.0000.000
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 head0.246
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