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Record W2007839411 · doi:10.1021/ja0725652

Enhancing Electron Accepting Ability of Triarylboron via π-Conjugation with 2,2‘-Bipy and Metal Chelation:  5,5‘-Bis(BMes<sub>2</sub>)-2,2‘-bipy and Its Metal Complexes

2007· article· en· W2007839411 on OpenAlexafffund
Yi Sun, Shu‐Bin Zhao, K. Huszarik, Wen‐Li Jia, Rui‐Yao Wang, Donal H. Macartney, Suning Wang

Bibliographic record

VenueJournal of the American Chemical Society · 2007
Typearticle
Languageen
FieldChemistry
TopicOrganoboron and organosilicon chemistry
Canadian institutionsQueen's University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryLigand (biochemistry)ChelationMetalFluorideMetal ions in aqueous solutionAdductInorganic chemistryMedicinal chemistryLewis acids and basesOne-electron reductionStereochemistryCrystallographyElectrochemistryOrganic chemistryPhysical chemistryCatalysis

Abstract

fetched live from OpenAlex

The synthesis of a new diboron compound, 5,5‘-bis(BMes 2 )-2,2‘-bipy (B2bipy, 1 ), has been accomplished. The conjugation of the 2,2‘-bipy unit with the two BMes 2 groups in 1 has been found to greatly enhance the electron-accepting ability of the boron centers, compared to the biphenyl analogue. 1 is an effective chelate ligand for metal ions and three metal complexes; namely, [Cu I (B2bipy)(PPh 3 ) 2 ][BF 4 ], 2, Pt II (B2bipy)Ph 2, 3a, and Pt II (B2bipy)Me 2, 3b, have been synthesized. The binding of metal ions to B2bipy was found to further significantly increase the electron-accepting ability/Lewis acidity of the boron centers. Cyclic voltammetry diagrams revealed that the free ligand and all three complexes display two reversible reduction peaks that are separated by 0.31−0.40 V. The first reduction potential ( E 1/2 ) for 1, 2, 3a, and 3b was found to be −1.69, −1.36, −1.34, and −1.38 V, respectively, versus FeCp 2 +/0 in DMF, which supports that the electron-accepting ability of the metal complexes is much greater than that of BMes(C 6 F 5 ) 2 . The strong electron-accepting ability/Lewis acidity of the metal complexes and the free ligand was manifested by their ability to sequentially bind to 2 equiv of F - ions in non-alcoholic solvents with K 1 ≥ 10 8 and 10 9 M -1 for 1 and 3a, respectively, and to 1 equiv of F - ions in the presence of methanol/ethanol or water. The crystal structures of 1, its 2:1 fluoride adduct [NBu 4 ] 2 [ 1F 2 ], and 3a were established by X-ray diffraction analyses. The 1:1 fluoride adduct of 2, [Cu I (B2bipyF)(PPh 3 ) 2 ], 2F, isolated directly from the reaction of 2 with NBu 4 F in a 4:1 mixture of CH 3 OH and CH 2 Cl 2 was characterized. All metal complexes are intensely colored and display a characteristic metal-to-ligand (B2bipy) charge transfer absorption band in the visible region, which was found to be highly sensitive toward binding by anions such as fluorides.

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 score0.923

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 studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
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 head0.007
GPT teacher head0.239
Teacher spread0.233 · 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

Citations169
Published2007
Admission routes2
Has abstractyes

Explore more

Same venueJournal of the American Chemical SocietySame topicOrganoboron and organosilicon chemistryFrench-language works237,207