MétaCan
Menu
Back to cohort
Record W1979021826 · doi:10.1002/ejoc.200800187

Nucleohomolytic Substitution at Boron: A Computational Approach

2008· article· en· W1979021826 on OpenAlexaff
Claudio Carra, J. C. Scaiano

Bibliographic record

VenueEuropean Journal of Organic Chemistry · 2008
Typearticle
Languageen
FieldChemistry
TopicRadical Photochemical Reactions
Canadian institutionsUniversity of Ottawa
Fundersnot available
KeywordsChemistryLone pairNucleophileBoronNucleophilic substitutionSubstitution reactionOxygenMechanism (biology)Reaction mechanismComputational chemistryAlkylStereochemistryOxygen atomMedicinal chemistryPhotochemistryOrganic chemistryMoleculeCatalysis

Abstract

fetched live from OpenAlex

Abstract A theoretical investigation is reported on the reaction mechanism for oxygen‐centered radical attack on alkyl‐ and arylborane substrates. The model reveals how the mechanism, traditionally considered as a S H 2 reaction, involves instead nucleophilic attack of the oxygen lone pair on the empty boron p orbital. The single electron on the oxygen is not directly involved in the process, however, as a result of a stereoelectronic effect: the bond aligned with the SOMO orbital is deactivated and the corresponding ligand leaves promptly as a radical species. The overall mechanism can be described as a nucleohomolytic reaction that shares many characteristics with conventional nucleophilic substitution. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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 categoriesInsufficient 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 score0.117
Threshold uncertainty score0.995

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0060.000

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 head0.016
GPT teacher head0.205
Teacher spread0.189 · 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

Citations31
Published2008
Admission routes1
Has abstractyes

Explore more

Same venueEuropean Journal of Organic ChemistrySame topicRadical Photochemical ReactionsFrench-language works237,207