A practical synthesis and X-ray crystal structure of (E)-4-(1-naphthylvinyl)pyridine and related compounds
Why this work is in the frame
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Bibliographic record
Abstract
The synthesis, structure, and photoreactivity of (E)-4-(1-naphthylvinyl)pyridine ((E)-4-1-nvp; 1) and its coordination compounds have been investigated. Synthesis of (1) via Wittig olefination resulted in a challenging isomer separation and purification process. By synthesizing (1) via a Horner–Wadsworth–Emmons reaction, high stereoselectivity and purity were achieved. The crystal structure of (1) revealed significant intramolecular rotation facilitated by CH···π interactions, ultimately preventing olefin stacking in both the solid-state structure of (1) and a cocrystal with a structural isomer. Novel Ag(I) and Zn(II) coordination complexes that utilize (1) as a ligand were also synthesized and fully characterized, facilitating the examination of the relationship between molecular planarity and secondary bonding contributions via Hirshfeld surface analyses. These findings deepen our understanding of intermolecular interactions involving (E)-4-1-nvp and offer insights for designing novel photoresponsive materials capable of solid-state [2 + 2] cycloaddition.
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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 | 0.001 |
| 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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 it