Synthesis, characterization, and crystal structures of four 1,3-diisopropylbenzimidazolium salts with iodide, aluminum tetraiodide, tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate, and triiodide anions
Bibliographic record
Abstract
Four 1,3-disubstituted benzimidazolium salts: 1,3-diisopropylbenzimidazolium iodide (1), 1,3-diisopropylbenzimidazolium aluminum tetraiodide (2), 1,3-diisopropylbenzimidazolium triiodide (3), and 1,3-diisopropylbenzimidazolium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (4) have been characterized using single X-ray diffraction analysis. Compounds 2–4 are new and are characterized by NMR and IR spectroscopy. Compound 2 was prepared by reacting 1 with aluminum triiodide and compound 4 in a metathesis reaction of 1 with sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, giving yields of 96% and 93%, respectively. Compound 3 was prepared by reacting 1 with 1 eq. of iodine and was isolated in 34% yield. Compound 1 crystallizes in the Orthorhombic space group P212121 with an asymmetric unit consisting of one benzimidazolium cation and one iodine anion. Compound 2 crystallizes in the Monoclinic space group P21/ n with an asymmetric unit consisting of one benzimidazolium cation and one aluminum tetraiodide anion. Compound 3 crystallizes in the Monoclinic space group C2/ c with an asymmetric unit consisting of one and one-half benzimidazolium cations and one and one-half triiodide anions. Compound 4 crystallizes in the Triclinic space group P-1 with an asymmetric unit consisting of one benzimidazolium cation and one tetrakis[3,5-bis(trifluoromethyl)phenyl]borate anion. The NCN angles in all four compounds are approximately 110°, which is consistent with literature values. Stacking and halogen and hydrogen bonding interactions in the series are also discussed.
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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 | 0.001 | 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".