<i>meso</i>-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane as a building block in supramolecular chemistry; salts formed with 2,2′-biphenol, 4,4′-biphenol, 4,4′-thiodiphenol, 4,4′-sulfonyldiphenol, 3- and 4-hydroxybenzoic acids, 3,5-dihydroxybenzoic acid and phenylphosphonic acid; supramolecular structures in zero, one, two and three dimensions
Why this work is in the frame
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Bibliographic record
Abstract
The structure of meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-2,2'-biphenol (1/2), (C16H36N4).(C12H10O2)2 (1), is a salt [C16H38N4]2+.2[HOC6H4C6H4O]-: the cations are centrosymmetric with two protons held within the N4 cavity of the macrocycle by N-H...N hydrogen bonds, and the phenolate anions contain intramolecular O-H...O-hydrogen bonds. The ions are linked into a finite centrosymmetric aggregate by means of N-H...O hydrogen bonds. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-4,4'-thiobiphenol-methanol (1/2/2), (C16H36N4).(C12H10O2S)2.(CH4O)2 (2), and meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-4,4'-sulfonylbiphenol-methanol (1/2/2), (C16H36N4).(C12H10O4S)2.(CH4O)2 (3), are isomorphous: each is a salt, [C16H38N4]2+.2[HOC6H4SC6H4O]-.2MeOH (2) and [C16H38N4]2+.2[HOC6H4SO2C6H4O]-.2MeOH (3), and in each the phenolate anions are linked by O-H...O- hydrogen bonds into chains; antiparallel pairs of chains are cross-linked by the cations to form molecular ladders, with neutral methanol molecules acting as spacer units. In meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-3-hydroxybenzoic acid-methanol (1/2/2) (4), 3-hydroxybenzoate anions form chains, again cross-linked in pairs by the [C16H38N4]2+ cations to form molecular ladders, different from those in (2) and (3) in that the neutral methanol units are pendent from the ladders, rather than forming a part of it. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-4-hydroxybenzoic acid-methanol (1/2/1) (5) is again a salt, [C16H38N4]2+.2[HOC6H4COO]-.MeOH: chains of 4-hydroxybenzoate anions are continuously cross-linked by two different types of [C16H38N4]2+ cation into a two-dimensional net. Only one of the two types of cation is linked to the chains via neutral methanol spacer units. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-phenylphosphonic acid-water (1/4/2) (6) is a salt, [C16H40N4]4+.4[C6H5PO3H]-.2H2O, containing the centrosymmetric tetraprotonated amine units, which have a conformation quite different from the trans-III conformation uniformly found in the [C16H38N4]2+ cations. The phenylphosphonate anions and the water molecules are linked into chains of fused rings, which are linked by the cations into two-dimensional nets. In meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetrade cane-3,5-dihydroxybenzoic acid (1/2) (7), the 3,5-dihydroxybenzoate anions in the unsolvated salt [C16H38N4]2+.2[(HO)2C6H3COO]- are linked into continuous two-dimensional nets, which are in turn linked by the centrosymmetric cations to form a three-dimensional framework. meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclo tetradecane-4,4'-biphenol (1/3) (8) is a salt containing both neutral and anionic biphenol units, [C16H38N4]2+.2[HOC6H4-C6H4O]-.[HOC6H4C6H4OH]. The two types of biphenol unit form two-dimensional nets and these nets are linked by the cations to form three independent, three-dimensional frameworks which are fully interwoven, but not bonded to one another.
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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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.002 | 0.002 |
| Meta-epidemiology (broad) | 0.002 | 0.000 |
| Bibliometrics | 0.001 | 0.003 |
| Science and technology studies | 0.001 | 0.004 |
| Scholarly communication | 0.001 | 0.002 |
| Open science | 0.002 | 0.001 |
| Research integrity | 0.001 | 0.002 |
| 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 it