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Record W2290687190 · doi:10.1139/cjc-2015-0435

Complexes of trimethylsilyl trifluoromethanesulfonate with nitrogen, oxygen, and phosphorus donors

2016· article· en· W2290687190 on OpenAlexafffundvenue
Alasdair P. M. Robertson, Saurabh S. Chitnis, Seth Chhina, Harikrishnan.P.S. Harikrishnan.P.S., Brian O. Patrick, Hilary A. Jenkins, Neil Burford

Bibliographic record

VenueCanadian Journal of Chemistry · 2016
Typearticle
Languageen
FieldChemistry
TopicSynthesis and characterization of novel inorganic/organometallic compounds
Canadian institutionsMcMaster UniversityUniversity of British ColumbiaUniversity of Victoria
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryTrifluoromethanesulfonateTrimethylsilylSteric effectsLigand (biochemistry)Lewis acids and basesNitrogenNuclear magnetic resonance spectroscopyIonic bondingMedicinal chemistryCrystallographyStereochemistryIonCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

The Lewis acceptor chemistry of Me3SiOTf with p-block Lewis bases has been explored and a library of complexes has been characterized by spectroscopic and, where possible, crystallographic methods. Compounds with the generic formula [Me3Si(L)][OTf] (L = 4-dmap, pyr, imz, OPMe3, OPCy3, OPPh3, OpyrMe, dmso, PMe3) were isolated from 1:1 mixtures of Me3SiOTf and the respective ligand in CH2Cl2. Characterization by NMR spectroscopy confirmed the solution stability of all but [Me3Si(PMe3)][OTf], with indications that the latter dissociates into PMe3 and Me3SiOTf. Solid-state structures of [Me3Si(4-dmap)][OTf], [Me3Si(pyr)][OTf], [Me3Si(OPCy3)][OTf], [Me3Si(OPPh3)][OTf], [Me3Si(OpyrMe)][OTf], and [Me3Si(PMe3)][OTf] were elucidated by single crystal X-ray diffraction, confirming the envisaged ionic formulations resulting from the displacement of the OTf anion from the silicon center of Me3SiOTf by the incoming ligand. Mixtures of Me3SiOTf with other related donors, including ChPPh3 (Ch = S or Se), NEt3, SMe2, PPh3, 2,2′-bipy, or Me2CO, show no evidence of reaction under ambient conditions, reflecting the lower basicity and (or) greater steric encumbrance of these ligands. Reactions of Me3SiOTf with bis-donor ligands yielded complexes of the generic formulae [Me3Si(L–L)SiMe3][OTf]2 (L–L = 4,4′-bipy, tmeda, dmpe) and [Me3Si(L–L)][OTf] (L–L = 4,4′-bipy, tmeda, dmpe). The tmeda and dmpe complexes, however, were found to dissociate in solution, with complexes only prevailing in the solid phase. X-ray diffraction studies of [Me3Si(4,4′-bipy)SiMe3][OTf]2 and [Me3Si(dmpe)SiMe3][OTf]2 confirmed the expected connectivities and ionic formulations, with Si–ligand bond lengths comparable to those observed in [Me3Si(pyr)][OTf] and [Me3Si(PMe3)][OTf], respectively.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.002
Threshold uncertainty score0.006

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
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)0.0020.000

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 head0.010
GPT teacher head0.188
Teacher spread0.178 · 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 source (direct Gemma or distilled Codex), 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

Citations22
Published2016
Admission routes3
Has abstractyes

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