A Computational Study of the Isomerization of Prolyl Amides As Catalyzed by Intramolecular Hydrogen Bonding
Bibliographic record
Abstract
The cis-trans isomerization of N -acetylproline methylamide has been investigated by density functional theory. The introduction of an electron-withdrawing group at the C γ of proline has notable geometrical and energetic consequences on the cis-trans isomerization. In the presence of the fluoro and hydroxy substituents, the preferred mode of rotation of the acetyl group is in a counterclockwise direction, assisting in the formation of an N ... HN intramolecular hydrogen bond in the transition structures and enhancing the pyramidalization of the prolyl nitrogen. This study illustrates the important role the intramolecular N ... HN hydrogen bond plays in the cis-trans isomerization of proline-containing molecules and the catalytic possibilities of hydrogen bonding.
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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 | 0.000 |
| 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 | 0.000 | 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".