Chiral <i>versus</i> racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines
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Bibliographic record
Abstract
In the 1:1 adducts C(12)H(10)N(2).C(4)H(6)O(6) formed between 1,2-bis(4'-pyridyl)ethene and racemic tartaric acid [(I), triclinic P1;, Z' = 1] and (2R,3R)-tartaric acid [(II), triclinic P1, Z' = 2], the ionic components are linked by hard hydrogen bonds into single sheets, which are further linked by C-H.O hydrogen bonds. In the analogous adducts C(10)H(18)N(2).C(4)H(6)O(6) formed by 4,4'-bipyridyl with racemic tartaric acid [(III), triclinic P1;, Z' = 1] and the chiral acid [(IV), monoclinic P2(1), Z' = 1], the hard hydrogen bonds generate bilayers which are again linked by C-H.O hydrogen bonds. Piperazine forms a 1:1 salt [((C(4)H(10)N(2))H(2))(2+)].[(C(4)H(4)O(6))(2-)] with (2R,3R)-tartaric acid [(V), monoclinic P2(1)] sheets, which are linked by the cations to form a pillared-layer framework. In each of the 1:2 salts formed by racemic tartaric acid with piperazine [(VI), monoclinic P2(1)/n, Z' = 0.5] and 1,4-diazabicyclo[2.2.2]octane (DABCO) [(VII), monoclinic P2(1)/n, Z' = 0.5], the cation lies across a centre of inversion, with the [(HN(CH(2)CH(2))(3)NH)(2+)] cation disordered over two sets of sites: in both (VI) and (VII) the anions form a three-dimensional framework encapsulating large voids which accommodate the cations. The salt formed between DABCO and (2R,3R)-tartaric acid [(VIII), orthorhombic P2(1)2(1)2(1), Z' = 1] has 3:4 stoichiometry and contains four different types of ion, [(HN(CH(2)CH(2))(3)NH)(2+)](2).[N(CH(2)CH(2))(3)NH](+).3(C(4)H(5)O(6))(-).C(4)H(4)O(6)(2-): the hard hydrogen bonds generate a three-dimensional framework.
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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 | 0.003 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 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