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Record W4319864212 · doi:10.5267/j.ccl.2022.11.004

The global and local Reactivity of C,N-diarylnitryle imines in [3+2] cycloaddition processes with trans-β-nitrostyrene according to Molecular Electron Density Theory: A computational study

2023· article· en· W4319864212 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

venuePublished in a venue whose home country is Canada.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueCurrent Chemistry Letters · 2023
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsnot available
FundersAcademic Computer Centre Cyfronet, AGH University of Science and TechnologyInfrastruktura PL-Grid
KeywordsChemistryNitroalkeneRegioselectivityCycloadditionReactivity (psychology)ImineElectrophileNucleophileDensity functional theoryMedicinal chemistryComputational chemistryStereochemistryOrganic chemistryCatalysisEnantioselective synthesis

Abstract

fetched live from OpenAlex

The regioselectivity of the [3+2] cycloaddition reactions between trans-β-nitrostyrene and C,N-diarylnitryle imine analogues as three atom components (TACs) has been studied with the use of Conceptual Density Functional Theory in the framework of Molecular Electron density Theory. Global and local reactivity indices were determined. Presented quantum-chemical computations showed that, for the reaction of nitroalkene with diphenylnitryle imine, the most favourable reaction path is determined by the nucleophilic attack of C3 carbon atom of TAC on an electrophilic Cα carbon atom of nitroalkene. Therefore, the creation of 1,3,4-triphenyl-5-nitro-Δ2-pyrazoline, according to channel B, is more probable. Similarly, to presented conclusion, for reactions of nitroalkene with nitryle imines containing ED group at para position of the phenyl ring also the most favourable reaction paths run through channel B leading to 1,3,4-triphenyl-5-nitro-Δ2-pyrazolines. In turn, reactions of nitroalkene with nitryle imines containing EW group at para position of the phenyl ring have the opposite preference and the most favourable reaction paths is channel A leading to 1,3,5-triphenyl-4-nitro-Δ2-pyrazolines.

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.

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)0.000
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 score0.011
Threshold uncertainty score0.991

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.248
Teacher spread0.242 · 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