Molecular Tectonics. Hydrogen-Bonded Networks Built from Tetra- and Hexaanilines
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Bibliographic record
Abstract
A series of compounds with multiple PhNH 2 groups were synthesized and crystallized, and their structures were solved by X-ray diffraction to assess the ability of -NH 2 groups in anilines to direct molecular crystallization. 2,2‘,7,7‘-Tetraamino-9,9‘-spirobi[9 H -fluorene] ( 1c ) forms an inclusion complex held together in part by donation of hydrogen bonds from -NH 2 groups to guest molecules. Surprisingly, the -NH 2 groups do not engage in hydrogen bonding with each other. Tetrakis(4-aminophenyl)methane ( 2c ) crystallizes to form a guest-free close-packed diamondoid network in which each -NH 2 group donates and accepts one N−H···N hydrogen bond. Tetrakis[(4-aminophenoxy)methyl]methane ( 3c ), a more flexible analogue, also crystallizes as a close-packed structure maintained by an extensive network of N−H···N hydrogen bonds. Despite the structural similarity of tetraanilines 2c and 3c, their hydrogen-bonding patterns and network topologies are different. A flexible hexaaniline, 1,1‘-oxybis[3-(4-aminophenoxy)-2,2-bis[(4-aminophenoxy)methyl]]propane ( 4c ), produces a close-packed network joined by both N−H···N and N−H···O hydrogen bonds. Tetrakis(4-aminophenyl)ethylene ( 5 ) crystallizes as a hydrate to yield a structure consisting of layered hydrogen-bonded sheets. The diverse hydrogen-bonding motifs observed show that crystal engineering using direct interactions of the -NH 2 group of anilines is a challenging endeavor, and other intermolecular interactions can compete effectively with N−H···N hydrogen bonds to determine how crystallization occurs.
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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 | 0.000 |
| 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) | 0.000 | 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