Application of the Variable Oxygen Probe to Derivatives of 2,6-Dimethyltetrahydropyran-4-ol: Evidence for Through-Bond nO–σCC–σ*CO Interactions
Bibliographic record
Abstract
The variable oxygen probe has been applied to axial and equatorial 4-pyranols 4 and 5 and their ester and ether derivatives. Plots of C–OR bond distance versus pKa (ROH) provided evidence for slightly stronger donation into the σ*C–OR antibonding orbital in the equatorial derivatives 5 than in the axial derivatives 4, which is consistent with the presence of a through-bond nO–σCC–σ*CO interaction in 5. Evidence in support of this interpretation was also provided by density functional theory (DFT) calculations and natural bond orbital (NBO) analyses of the various orbital interactions in the 4-pyranols 4 and 5, their protonated analogues 4·H2O+ and 5·H2O+, and the corresponding cyclohexane derivatives 6, 7, 6·H2O+, and 7·H2O+.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".