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Record W2014725288 · doi:10.1021/om100563m

Dihydrogen Activation by B(<i>p</i>-C<sub>6</sub>F<sub>4</sub>H)<sub>3</sub> and Phosphines

2010· article· en· W2014725288 on OpenAlexaff
Matthias S. Ullrich, Alan J. Lough, Douglas W. Stephan

Bibliographic record

VenueOrganometallics · 2010
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryAdductBoraneSteric effectsMedicinal chemistryStereochemistryFrustrated Lewis pairHydrideReagentLewis acids and basesMetalCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

The Grignard reagent ( p -C 6 F 4 H)MgCl was used to prepare (Et 2 O)B( p -C 6 F 4 H) 3 ( 2 ) and the free borane B( p -C 6 F 4 H) 3 ( 1 ). On the basis of Lewis acidity tests, the borane 1 exhibits ca. 95% of the acidity of B(C 6 F 5 ) 3 . 1 forms classical adducts with ethers and phosphines of the general formula (L)B( p -C 6 F 4 H) 3 (L = Et 2 O ( 2 ), THF ( 3 ), Me 3 P ( 4 ), Et 3 P ( 5 ), i -Pr 2 (H)P ( 6 ), Ph 3 P ( 7 ), (3,5-Me 2 C 6 H 3 ) 3 P ( 8 ), t -Bu 2 (H)P ( 9 ), and Cy 3 P ( 10 )). Compounds 9 and 10 react with 4 atm of H 2 to give the salts [ t -Bu 2 PH 2 ][HB( p -C 6 F 4 H) 3 ] ( 11 ) and [Cy 3 PH][HB( p -C 6 F 4 H) 3 ] ( 12 ). The sterically demanding phosphines R 3 P (R = t -Bu, i -Pr, 2,4,6-Me 3 C 6 H 2, and 2-MeC 6 H 4 ), R 2 R′P (R,R′ = t -Bu, i -Pr and t -Bu, Cy), and (Ph 2 CH)R 2 P (R = t -Bu ( 22 ), i -Pr ( 23 ), Cy ( 24 ), and C 5 H 9 ( 25 )) show no evidence of adduct formation with 1, but react with H 2 to give the corresponding salts [R 3 PH][HB( p -C 6 F 4 H) 3 ] ( 13 − 16 ), [R 2 R′PH][HB( p -C 6 F 4 H) 3 ] ( 17 − 20 ), and [(Ph 2 CH)R 2 PH][HB( p -C 6 F 4 H) 3 ] ( 26 − 29 ), respectively. The [ t -Bu 2 PH 2 ] + species 11 is stable only under an H 2 overpressure, while the [ t -Bu 3 PH] + salt 13 cleanly extrudes isobutene and H 2 at elevated temperatures to give 9 . The [(2-MeC 6 H 4 ) 3 PH] + derivative 16 readily liberates H 2 under vacuum, thus providing a metal-free system capable of reversible H 2 uptake and release. Crystallographic data for compounds 1, 5, 8, 9, 10, 13, and 26 are 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.

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity
Consensus categoriesMeta-epidemiology (narrow)
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 score0.014
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0010.001
Scholarly communication0.0000.001
Open science0.0010.001
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0010.000

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 head0.005
GPT teacher head0.197
Teacher spread0.191 · 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; both teacher heads agree on what is shown here.

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

Citations91
Published2010
Admission routes1
Has abstractyes

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