Catalysis Mediated by Hydrogen Bonding: A Computational Study of the Aminolysis of 6-Chloropyrimidine
Bibliographic record
Abstract
Density functional theory has been employed to investigate the effects of hydrogen bonding on the aminolysis of 6-chloropyrimidine, i.e., the reaction of NH 3 with 6-chloropyrimidine to give HCl and 6-aminopyrimidine. The isolated aminolysis of 6-chloropyrimidine requires 138.1 kJ mol - 1 . If the electron-donating species H 2 CO is hydrogen bonded to the NH 3 moiety during aminolysis, the barrier is reduced to 112.2 kJ mol - 1 . When H 2 NCHO is added to NH 3 + 6-chloropyrimidine, the electron-donating −CHO group is able to hydrogen bond to the NH 3 moiety while the electron-accepting −NH 2 group hydrogen bonds to the N of the pyrimidine ring that is adjacent to the carbon at which substitution occurs. This results in the barrier to aminolysis of 6-chloropyrimidine being reduced to 95.3 kJ mol - 1 . Thus, the aminolysis of 6-chloropyrimidine, as mediated by hydrogen bonding, provides a clear and simple example of the catalytic possibilities of well-chosen 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) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.001 |
| 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".