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Record W2073421726 · doi:10.1002/ejic.201100698

Radical Chemistry of Iminepyridine Ligands

2011· article· en· W2073421726 on OpenAlexaff
Peter H. M. Budzelaar

Bibliographic record

VenueEuropean Journal of Inorganic Chemistry · 2011
Typearticle
Languageen
FieldChemistry
TopicOrganometallic Complex Synthesis and Catalysis
Canadian institutionsUniversity of Manitoba
Fundersnot available
KeywordsChemistryAlkylSteric effectsUnpaired electronDissociation (chemistry)IminePyridineReactivity (psychology)AlkylationLigand (biochemistry)Electron transferMedicinal chemistryRegioselectivityBond-dissociation energyMetalPhotochemistryStereochemistryRadicalOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract The reactivity of metal fragments MeLi(THF), Me 2 Mg, Me 2 Zn and Me 3 Al with a variety of imine/pyridine ligands was studied by DFT methods. Ligands having at least two such groups in conjugation very effectively accept an electron from a metal–carbon bonding orbital and thus assist alkyl dissociation: the M–Me dissociation free energy Δ G d decreases by about 45 kcal/mol for the Li, Mg and Zn fragments, and by 60–70 kcal/mol for Me 3 Al. Paths for transfer of an alkyl group to the ligands were also explored. Paths for transfer to ligand carbon atoms were found to have high barriers, and such transfers are instead proposed to proceed via initial M–Me dissociation. Direct alkyl transfer to ligand nitrogen atoms is somewhat easier, and for the most electropositive metal Li such a transfer might compete with radical chemistry. For Dimpy, the most stable products are the C3 and C4 alkylation ones. However, the observed regioselectivity of alkyl transfer (often to N py or C2) does not correlate with product stability and is likely to be a complicated function of radical stability, steric factors and unpaired electron density distribution. The results illustrate that Dimpy and related ligands should be considered strong, reversible oxidants.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
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 score0.151
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.1060.000

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 head0.019
GPT teacher head0.192
Teacher spread0.173 · 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

Citations40
Published2011
Admission routes1
Has abstractyes

Explore more

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