Chemistry of the potassium, silver, and tetra(<i>n</i>-butyl)ammonium salts of sydnone <i>N</i>-oxide (Traube's anion)
Bibliographic record
Abstract
Traube's dianion, 4-methylcarboxysydnone-3-hydroxylate (2), and its monomethyl ester (1) are readily isolated as their di- and mono-potassium salts from the reaction of nitric oxide with dimethylmalonate and potassium methoxide in methanol. Metathesis reactions of 1 with silver nitrate and tetra(n-butyl)ammonium bromide yield the silver and tetra(n-butyl)ammonium salts of 4-methylcarboxysydnone-3-hydroxylate. In contrast to other known sydnone derivatives, the present sydnones are stable in both acidic and basic solutions. Single crystal X-ray diffraction data obtained for 2 and the silver salt (3) reveal planarity and delocalization of double bonds in the sydnone ring, indicating aromatic behavior. The tetra(n-butyl)ammonium salt (4) is soluble in a range of organic compounds. Cyclic voltammetric data measured for 4 in acetonitrile reveal an irreversible oxidation peak at +1.09 V vs. Fc–Fc+ couple suggesting that the sydnone derivatives can be oxidized with an appropriate oxidizing agent. Differential scanning calorimetry data reveal thermal stability at ambient conditions and exothermic decomposition at high temperatures (>229 °C). The sydnone derivatives are characterized by two strong electronic absorptions in the UV region and rich vibrational (IR and Raman) spectra in the 1800–1500 cm–1 region. Density functional theory (B3LYP/6-311+++G**) is applied to estimate the aromaticity of the sydnone ring and to assign the vibrational spectral data.Key words: sydnone, trans-diazeniumdiolate, N-oxide.
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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 | 0.000 | 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) | 0.001 | 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".