Rationalization of Diels–Alder reactions through the use of the dual reactivity descriptor Δf(r)
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.
Bibliographic record
Abstract
In this work, the dual descriptor of chemical reactivity, an electronic density-based index, is used to study both the regioselectivity and the stereoselectivity of Diels-Alder reactions. The descriptor has been designed to simultaneously delineate the nucleophilic and electrophilic sites within a molecule. Subsequent pairing between the nucleophilic and electrophilic regions of the reagents predicts the major adducts in all cases studied. Specifically, the descriptor predicts the generation of a ortho-regioisomer when a diene monosubstitued at position 1 by an Electron Donating Group (EDG)/Electron Withdrawing Group (EWG), reacts with a dienophile monosubtituted by an EWG/EDG. Under the same conditions, if the diene is monosubstituted by either an EWG or an EDG at position 2, formation of the para-oriented adduct is predicted. This approach also provides insight into the stereoselectivity. For example, secondary interactions between the non-reactive regions of the reactants explain why the endo stereoisomer is preferred.
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 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 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| 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 it