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Record W4411977914 · doi:10.1021/acs.joc.5c00730

Exploring Triel Bonding to Halogens for More Potent σ-Holes

2025· article· en· W4411977914 on OpenAlexafffund
Roxanne Dekeyser, Travis Dudding

Bibliographic record

VenueThe Journal of Organic Chemistry · 2025
Typearticle
Languageen
FieldMaterials Science
TopicBoron and Carbon Nanomaterials Research
Canadian institutionsBrock University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsHalogen bondHalogenChemistryNanotechnologyMaterials scienceOrganic chemistry

Abstract

fetched live from OpenAlex

Noncovalent interactions are indispensable to chemical science and crucial to fostering new perspectives on molecular structure and reactivity. In this pursuit, halogen bonding has been the object of much attention in recent years, and strategies to enhance and control this noncovalent force are highly sought. In shaping this area, we show here neutral and cationic boron centers through triel bond donor–acceptor X → B (X = Cl, Br, I) interactions allow for enhanced halogen bonding. Central to this concept is donation from the electron-rich belt of a halogen atom to an electron deficient boron center achieved by peri -proximity on a naphthyl scaffold. As shown in this study, such interactions are capable of enhancing the halogen bonding ability by more than 7 kcal/mol. To further probe this effect, experimental studies demonstrating the power of this interaction for catalysis are offered in the context of imine reduction. Overall, this experimental and computationally based study contributes to the development of fundamental aspects of organoboron chemistry and halogen bonding.

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 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 score0.004
Threshold uncertainty score0.364

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
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 science0.0010.000
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 head0.061
GPT teacher head0.302
Teacher spread0.241 · 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.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations2
Published2025
Admission routes2
Has abstractyes

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