Protonolysis of BH<sub>4</sub><sup>–</sup> Leads to Intermediacy of BH<sub>3</sub>-σ(H<sub>2</sub>) That Evolves H<sub>2</sub> and Furnishes Borane as the Key Reducing Agent
Bibliographic record
Abstract
Borohydride (BH 4 – ) is a ubiquitous reducing agent in chemistry despite its apparent inability to transfer hydride fragments without assistance. In protic solvents such as methanol, B–H protonolysis and H 2 evolution furnish borane, which serves as the key hydride delivery agent in the reduction of cyclohexanone. Contrasting with widely accepted but inaccessible mechanisms involving direct (intermolecular) hydride transfer from BH 4 –, in this work, DFT calculations performed in close conjunction with H/D exchange studies unambiguously justify the use of alcohol as a necessary evil that renders substantial kinetic advantages in intramolecular hydride transfer, albeit requiring excess BH 4 – to compensate for the protonolytic loss of available B–H fragments as H 2 .
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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 | 0.003 | 0.001 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.002 | 0.001 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.001 | 0.001 |
| Open science | 0.002 | 0.002 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.000 | 0.002 |
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; both teacher heads agree on what is shown here.
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".