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Record W4409360104 · doi:10.1139/cjc-2024-0242

The first organometallic 1,3,4-oxathiazol-2-one and a comprehensive crystallographic and computational survey of the effects of various 5 substituents

2025· article· en· W4409360104 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.
venuePublished in a venue whose home country is Canada.

Bibliographic record

VenueCanadian Journal of Chemistry · 2025
Typearticle
Languageen
FieldChemistry
TopicSynthesis and Reactivity of Sulfur-Containing Compounds
Canadian institutionsCrandall UniversityUniversity of FrederictonUniversity of New BrunswickSaint Mary's University
FundersNatural Sciences and Engineering Research Council of CanadaNew Brunswick Innovation FoundationSaint Mary’s University
KeywordsChemistryCrystallographyStereochemistryComputational chemistry

Abstract

fetched live from OpenAlex

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.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Observational · Consensus signal: Observational
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.412
Threshold uncertainty score0.371

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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.

Opus teacher head0.008
GPT teacher head0.195
Teacher spread0.187 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it