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Record W2540385322 · doi:10.1139/cjc-2016-0334

Is (benzene)Cr(CO)<sub>3</sub> really more aromatic than benzene?

2016· article· en· W2540385322 on OpenAlexvenueno aff
Amnon Stanger

Bibliographic record

VenueCanadian Journal of Chemistry · 2016
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Properties of Aromatic Compounds
Canadian institutionsnot available
FundersIsrael Science Foundation
KeywordsCyclobutadieneBenzeneAntiaromaticityChemistryAnnuleneAromaticityRing (chemistry)Chemical shiftComputational chemistryPhysical chemistryOrganic chemistryMolecule

Abstract

fetched live from OpenAlex

(benzene)Cr(CO)3 was claimed to be more aromatic than benzene, based on the central 1H Me chemical shifts in dimethyldihydropyrene annulated to it. In this paper, several dihydropyrenes are computationally investigated. NICS-scan methods are used to assess the ring current properties, and NMR calculations are used for obtaining NMR chemical shifts. The parent and four benz-annulated dihydropyrenes show excellent agreement with the experimental results, reported by R. Mitchell in several papers. The effect of annulating the antiaromatic cyclobutadiene was shown to be larger than that of benzene and to change the type of ring currents; while benz-annulated dihydropyrenes maintain local 14-annulene and local benzenic ring currents, the cyclobutadiene-annulated dihydropyrenes show global (and local) ring currents. A NICS-scan study of (benzene)Cr(CO)3 and a NICS-XY-scan study of the (CO)3Cr(C6H4)-annulated to dihydropyrene show that the benzene in the Cr complex is at most aromatic as benzene, probably somewhat less. A detailed study of the 1H chemical shifts suggests that the experimental results were somewhat misinterpreted, and that (benzene)Cr(CO)3 is at most as aromatic as benzene.

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 score0.004
Threshold uncertainty score0.008

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 studies0.0000.001
Scholarly communication0.0010.001
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 head0.014
GPT teacher head0.207
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
Published2016
Admission routes1
Has abstractyes

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Same venueCanadian Journal of ChemistrySame topicSynthesis and Properties of Aromatic CompoundsFrench-language works237,207