Comparative Study of Predicting Radical CH Functionalization Sites in Nitrogen Heteroarenes Using a Radical General‐Purpose Reactivity Indicator and the Radical Fukui Function
Bibliographic record
Abstract
ABSTRACT The Radical General‐Purpose Reactivity Indicator (R‐GPRI) is a valuable new tool for discerning the most reactive atoms within a molecule undergoing radical attack. In this study, we apply the condensed R‐GPRI and the condensed Radical Fukui Function (RFF) to identify the two most reactive atoms in 14 nitrogen heteroarenes subjected to radical attack by •CF 3 (trifluoromethyl radical) and • i ‐Pr (isopropyl radical). The results were compared with available experimental data and calculated activation barriers to comprehensively evaluate the reactivity of these molecules, especially in reactions without isolated products. The outcomes indicate that R‐GPRI is a robust alternative for identifying the most reactive CH sites in disubstituted nitrogen heteroarenes, outperforming the RFF. We also found that for nitrogen heteroarenes, summing the charges of the hydrogen atoms into the heavier atoms to which they are bonded as computed with the Hirshfeld population scheme enhances the performance of the RFF compared to previous findings. As such, the R‐GPRI appropriately incorporates both charge and RFF contributions. It is also observed that the atoms within molecules that have a small condensed RFF tend to be unreactive in these radical attack reactions. This is even observed in atoms with the largest charge in magnitude (with the appropriate sign) but a small condensed RFF.
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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".