The first organometallic 1,3,4-oxathiazol-2-one and a comprehensive crystallographic and computational survey of the effects of various 5 substituents
Bibliographic record
Abstract
The crystal structures and chemistry of the 1,3,4-oxathiazol-2-one ring is explored by the synthesis and crystal structures of four derivatives bearing a diverse selection of substituent groups. These compounds expand the families with sp 3 alkyl substitution and bis-oxathiazolones (1), thiophenes (3), along with the first ever example of a true organometallic coordination compound substituted oxathiazolone featuring a ferrocene substituent (4). Decomposition of the ferrocene derivative into the corresponding nitrile (5) represents the first time an oxathiazolone and its nitrile have been fully characterized including crystallographic analysis in the same study. The crystal structures of 1,8-bis(1′,3′,4′-oxathiazol-2′-one-5′-yl) octane 1 and ethyl-2-oxo-1,3,4-oxathiazol-5-carboxylate 2 reveal the molecules arranged in co-planar, head to head chains, and dimers, respectively, directed by sulfur–oxygen contacts. 5-(1′,2′,3′,4′,5′-pentaphenylferrocenyl)-1,3,4-oxathiazol-2-one 4, presumably due to significant steric bulk of the pentaphenyl moiety, exists with minimal significant solid state oxathiazolone ring interactions aside from oxathiazolone carbonyl–phenyl proton hydrogen bonds. The crystal structure of 5-(2-methyl-3-thienyl)-1,3,4-oxathiazol-2-one 3 is co-planar, head to tail dimers oriented by S…O contacts between the carbonyl oxygen and the thienyl sulfur. A theoretical analysis of the physical and electronic structures of the four oxathiazolone derivatives opens an opportunity to address the sensitivity of the decomposition of the heterocycle to substituent effects.
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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) | 0.001 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.001 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.004 | 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".