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Record W2006895914 · doi:10.1021/ja9921423

Does Cr(CO)<sub>3</sub> Complexation Reduce the Aromaticity of Benzene?

2000· article· en· W2006895914 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 · 2000
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Properties of Aromatic Compounds
Canadian institutionsUniversity of Calgary
Fundersnot available
KeywordsCyclobutadieneAromaticityChemistryRing (chemistry)AntiaromaticityBenzeneRing currentDiamagnetismChromiumRing strainComputational chemistryCrystallographyMoleculeOrganic chemistryPhysics

Abstract

fetched live from OpenAlex

Ring currents in (C 6 H 6 )Cr(CO) 3, 1, ( cis -1,3-butadiene)Cr(CO) 4 ( 4 ), (C 6 H 6 ) 2 Cr ( 5 ), (C 4 H 4 )Fe(CO) 3 ( 6 ), and ( cis -1,3-butadiene)Fe(CO) 3 ( 8 ) have been assessed by σ−π disected nucleus independent chemical shift (NICS) calculations. Shielding contributions from the C−C(π) orbitals to the NICS values reveal that there is no quenching of ring current in the benzene ring of 1 or in dibenzene chromium 5 . The previously reported paratropic ring current for 1 is shown to be a consequence of latent aromaticity in 1,3-butadiene chromium tetracarbonyl 4 (one of the molecules used in the magnetic susceptibility equation). NICS values, a diatropic ring current, and a positive aromatic stabilization energy (ASE) all point to this aromaticity. NICS values for cyclobutadiene iron tricarbonyl, 6, show moderately sized diamagnetic shielding above the plane of the four-membered ring. In addition, 6 has a negative magnetic susceptibility exaltation (MSE) (diatropic ring current), quite opposite from the large paratropic current calculated for cyclobutadiene ( D 2 h ) itself. Evaluated using “strain corrected” isodesmic reactions, 6 has a large ASE in contrast to a large destabilization calculated for cyclobutadiene with the same equation. The 1,3-butadiene complex 8 also shows features of three-dimensional aromaticity, NICS(1) −8.7, NICS(1) π −2.8, and a moderate ASE stabilization energy (7.9 kcal/mol, eq 7), but this complex has a negligible MSE of −1.0 ppm cgs. We predict the ring current order to be the following: benzene ∼ 1 ∼ 5 > 6 > 4 > 8 .

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 score0.025
Threshold uncertainty score0.438

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.001
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0010.000
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 head0.014
GPT teacher head0.239
Teacher spread0.225 · 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