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Record W2012299949 · doi:10.1021/cg034134a

Supramolecular Grid and Layer Architectures. Hydrogen Bonds and Halogen−Halogen Interactions Influenced by Bromo-, Chloro-, and Cyano-Substituted Anilic Acids

2004· article· en· W2012299949 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueCrystal Growth & Design · 2004
Typearticle
Languageen
FieldChemistry
TopicCrystallography and molecular interactions
Canadian institutionsNational Research Council CanadaSteacie Institute for Molecular Sciences
Fundersnot available
KeywordsSupramolecular chemistryChemistryHydrogen bondChloranilic acidMoleculeHalogenCrystallographyHalogen bondAcetonitrileAcceptorSupramolecular assemblyIntermolecular forceMethanolStereochemistryCrystal structureAlkylOrganic chemistry

Abstract

fetched live from OpenAlex

Supramolecular reactions were performed between 2,2‘-bipyrimidine (BPM) and 2,5-substituted cyano- and haloanilic acids [cyananilic acid (CNA), chloranilic acid (ClA), and bromanilic acid, (BrA)] under identical reaction conditions in methanol and a mixture of acetonitrile and methanol. The cyano and hydroxyl functional units of CNA in supramolecular compound 1 are hydrogen-bonded through water molecules and form a two-dimensional network with a grid motif. The grid cavities are occupied by BPM molecules, which are strongly linked by water molecules that connect to the CNA network. The supramolecular architecture of 1 thus consists of a three-dimensional hydrogen-bonded network. The 1:1:2 (H 2 O) compound 2 has intermolecular O−H···O and O−H···N hydrogen bonds: (i) ClA···H 2 O···BPM linked along the diagonal line of the bc -plane and (ii) BPM···H 2 O···BPM connected along the b -axis. This structure includes strong Cl···Cl interactions at 3.34 Å, which generate a three-dimensional packing arrangement as strengthened by acid···acid interaction. A new class of hydrogen-bonded 1:1:4 (H 2 O) supramolecular compound 3 is formed from BPM, BrA, and water molecules, where structure formation is directed by O−H···O and O−H···N hydrogen bonds, as well as weaker C−H···O and C−H···Br interactions between BPM and BrA. Remarkable Br···Br interactions at 3.68 Å are observed that are similar to the Cl···Cl interactions in 2 . The three supramolecular compounds have been prepared with the specific aim of assessing a new donor−acceptor-type of hydrogen-bonded interactions to control the architecture of organic solids for the further invention of supramolecular solid-state materials.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.023
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

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.

Opus teacher head0.010
GPT teacher head0.225
Teacher spread0.216 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it