Formation and stability of organic zwitterions The carbon acid p<i>K</i><sub>a</sub>s of the trimethylsulfonium and tetramethylphosphonium cations in water
Bibliographic record
Abstract
We report second-order rate constants of k DO = 7.5 × 10 4 and 9.9 × 10 5 (mol/L) 1 s 1 for exchange for deuterium of the first methyl proton of the trimethylsulfonium and tetramethylphosphonium cations, respectively, in D 2 O at 25 °C and I = 1.0 (KCl). The data were analyzed to give the following carbon acidities for these cationic carbon acids in water: (CH 3 ) 3 S + , pK a = 28.5; (CH 3 ) 4 P + , pK a = 29.4. These acidities are close to those of the neutral carbon acids acetonitrile and dimethylacetamide. This provides evidence that a portion of the stabilization of the cyanomethyl carbanion is due to resonance delocalization of negative charge from carbon to cyano nitrogen.Key words: carbon acids, carbanions, ylides, proton transfer.
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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".