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Record W1991597389 · doi:10.1021/ja002901d

Nonplanar Aromatic Compounds. 5.<sup>1</sup> A Strategy for the Synthesis of <i>cis</i>-10b,10c-Dimethyl-10b,10c-dihydropyrenes. First Crystal Structure of a <i>cis</i>-10b,10c-Dimethyl-10b,10c-dihydropyrene

2001· article· en· W1991597389 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.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueJournal of the American Chemical Society · 2001
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Properties of Aromatic Compounds
Canadian institutionsMemorial University of Newfoundland
Fundersnot available
KeywordsChemistryAnnuleneValence (chemistry)Crystal structureCrystal (programming language)Alternation (linguistics)Cis–trans isomerismCrystallographyValence bond theoryComputational chemistryMoleculeStereochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Through the use of a potentially removable tether, a heavily substituted 10b,10c-dimethyl-10b,10c-dihydropyrene (DMDHP), 20, was synthesized exclusively as the cis-isomer. It exists as the major component (20:1) in an equilibrium with its valence isomer syn-[2.2]metacyclophanediene 19. An X-ray crystal structure determination of 20, a cis-(2,7)-10b,10c-dihydropyrenophane, provided the first experimental measurements of the cis-DMDHP skeleton. The observed bond alternation in the [14]annulene was found to be larger than that of the corresponding trans-DMDHP framework. Prior MMPI calculations, on which previous discussion of the structure of the cis-DMDHP system had been based, are in very good agreement with the experimental results. Our own DFT calculations predict a more symmetric and more bond equalized structure than was observed in 20.

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)0.002
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Science and technology studies
Consensus categoriesMeta-epidemiology (narrow)
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 score0.012
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0020.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0040.004
Bibliometrics0.0000.001
Science and technology studies0.0010.003
Scholarly communication0.0000.000
Open science0.0040.001
Research integrity0.0010.002
Insufficient payload (model declined to judge)0.0010.000

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 head0.013
GPT teacher head0.234
Teacher spread0.220 · 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