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Record W2313413640 · doi:10.1021/om5011462

Mechanisms of α-, β-, and γ-H(D) Exchange Processes in the α-Agostic Alkyltitanocene(IV) Complexes [Cp<sub>2</sub>TiCH<sub>2</sub>CH(CH<sub>3</sub>)(CMe<sub>3</sub>)]<sup>+</sup>and [Cp<sub>2</sub>TiCH<sub>2</sub>CH(CD<sub>3</sub>)(CMe<sub>3</sub>)]<sup>+</sup>: Stark Contrasts with Their γ-SiMe<sub>3</sub>Analogues

2015· article· en· W2313413640 on OpenAlexafffund
Alexandre F. Dunlop-Brière, Michael C. Baird, Peter H. M. Budzelaar

Bibliographic record

VenueOrganometallics · 2015
Typearticle
Languageen
FieldChemistry
TopicOrganometallic Complex Synthesis and Catalysis
Canadian institutionsUniversity of ManitobaQueen's University
FundersSaudi Basic Industries CorporationNatural Sciences and Engineering Research Council of CanadaQueen's UniversityCanada Foundation for Innovation
KeywordsAgostic interactionChemistryHydrideAlkeneIsotopologueSteric effectsIntramolecular forceStereochemistryMedicinal chemistryTetrahydrofuranCrystallographyHydrogenMoleculeMetalCatalysisOrganic chemistry

Abstract

fetched live from OpenAlex

The α-agostic alkyltitanocene(IV) complex [Cp 2 TiCH 2 CH(CH 3 )(CMe 3 )] + ( II ) and its D 3 isotopologue [Cp 2 TiCH 2 CH(CD 3 )(CMe 3 )] + ( II -CD 3 ) undergo reversible, intramolecular H–H(D) exchange among the α-, β-, and γ- (β-Me) positions of the alkyl ligands in addition to concomitant intermolecular H–H(D) exchange with the vinylic and 2-methyl sites of the product of β-hydrogen elimination, CH 2 ═CMeCMe 3, results which are in strong contrast to the exchange behavior of the γ-agostic silyl analogues [Cp 2 TiCH 2 CH(CH 3 )(SiMe 3 )] + ( III ) and [Cp 2 TiCH 2 CH(CD 3 )(SiMe 3 )] + ( III -CD 3 ). As has been previously shown, III undergoes tunnelling-expedited exchange of the β-H (but not α-H) with the hydrogen atoms of the β-methyl group (β-H/γ-H exchange) while III -CD 3 isomerizes reversibly but specifically to the isotopomer [Cp 2 TiCD 2 CD(CH 3 )(SiMe 3 )] +, forgoing β-H/γ-H exchange completely. In this paper we show that all of the exchange processes of II / II -CD 3 and III / III -CD 3 initially involve conventional β-H elimination processes and thus, at some stage, intermediacy of the corresponding hydrido alkene complexes [Cp 2 TiH(CH 2 ═CMeCMe 3 )] + ( VI ) or [Cp 2 TiH(CH 2 ═CMeSiMe 3 )] + (or their D 3 isotopologues). The major reason for the vastly different exchange behaviors of the two structurally very similar alkyltitanocene systems II and III is simply that, for steric and electronic reasons, the alkene in VI dissociates reversibly to the hydride, [Cp 2 TiH] +, and free alkene while that in [Cp 2 TiH(CH 2 ═CMeSiMe 3 )] + does not; CH 2 ═CMeSiMe 3 remains coordinated at the temperature and on the time scale of the experiments. DFT calculations generally support our mechanistic conclusions and furthermore point to a subtle ion pairing effect which hinders intramolecular η 2 -alkene rotation in VI and [Cp 2 TiH(CH 2 ═CMeSiMe 3 )] +, thereby exerting a surprisingly important, heretofore unanticipated, influence on the nature of the chemistry involved.

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)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
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 head0.019
GPT teacher head0.212
Teacher spread0.193 · 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

Citations6
Published2015
Admission routes2
Has abstractyes

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