MétaCan
Menu
Back to cohort

Unexpected reaction of antimony pentafluoride with a fluorinated propellane

2024· article· en· W4394789200 on OpenAlexfundno aff
Matthias Bremer

Bibliographic record

VenueJournal of Fluorine Chemistry · 2024
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsnot available
FundersUniversité de Sherbrooke
KeywordsChemistryPropellaneDicationAntimonyComputational chemistryIonMedicinal chemistryPhotochemistryExothermic reactionOrganic chemistryBicyclic molecule

Abstract

fetched live from OpenAlex

• Density functional calculations show. • Antimony pentafluoride or its dimer add in an exothermic fashion to strained organic molecules forming zwitterionic structures. • The ease of formation and the stability of these zwitterions is governed by the degree of fluorination of the organic moiety. • The elusive trishomoaromatic 1,3-dihydro-5-adamantyl cation might be generated in solution by hydride abstraction from 1,3-dehydroadamantane. While 1,3-dehydro-5,7-difluoroadamantane 11 reacts with SbF 5 in super acid media (SO 2 ClF) to generate the 1,3-dehydroadamant-5,7-diyl dication 1 , 1,3-dehydro-5-fluoroadamantane 12 fails to react analogously to produce the 1,3-dehydroadamant-5-yl cation 9 ; instead, the 3,5-difluoro-1-adamantylcation 13 is formed. We present a computational study that explains this surprising behavior by the initial addition of Sb 2 F 10 to the propellane bond present in 12 . This is computed to be highly exothermic and leads to a zwitterionic (or ion-pair) species, which in turn reacts autocatalytically with HF to produce the observed fluorinated cation 13 , SbF 3 , and SbF 6 – .

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 score0.047
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
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.002
Insufficient payload (model declined to judge)0.0020.000

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 head0.043
GPT teacher head0.378
Teacher spread0.335 · 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

Citations0
Published2024
Admission routes1
Has abstractyes

Explore more

Same venueJournal of Fluorine ChemistrySame topicFluorine in Organic ChemistryFrench-language works237,207