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 machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.002 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.002 | 0.001 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.001 | 0.001 |
| Open science | 0.002 | 0.001 |
| Research integrity | 0.002 | 0.001 |
| Insufficient payload (model declined to judge) | 0.003 | 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 source (direct Gemma or distilled Codex), 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".