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Record W2253172069 · doi:10.1021/acs.joc.5b02552

Engineering Hydrogen-Bonded Hexagonal Networks Built from Flexible 1,3,5-Trisubstituted Derivatives of Benzene

2016· article· en· W2253172069 on OpenAlexafffund
Fatima Helzy, Thierry Maris, James D. Wuest

Bibliographic record

VenueThe Journal of Organic Chemistry · 2016
Typearticle
Languageen
FieldChemistry
TopicCrystallography and molecular interactions
Canadian institutionsUniversité de Montréal
FundersUniversité de MontréalNatural Sciences and Engineering Research Council of CanadaCanada Research ChairsCanada Foundation for InnovationMinistère de l'Éducation, du Loisir et du Sport Québec
KeywordsChemistryHexagonal crystal systemBenzeneBenzene derivativesHydrogen bondHydrogenPolymer chemistryOrganic chemistryMoleculeCrystallographyChemical synthesis

Abstract

fetched live from OpenAlex

2,4-Diamino-1,3,5-triazinyl (DAT) groups are known to form N-H···N hydrogen bonds according to reliable patterns of self-association. In compounds 3a-c, three DAT groups are attached to trigonally substituted phenyl cores via identical flexible arms. Crystallization of compounds 3a-c produces robust networks in which each molecule is linked to its immediate neighbors by a total of 10-12 hydrogen bonds. In compound 3a, the DAT groups are designed to lie close to the plane of the phenyl core, thereby giving hydrogen-bonded sheets built from hexameric rosettes. In contrast, the more highly substituted phenyl cores of analogues 3b and 3c favor conformations in which the DAT groups are no longer coplanar, leading predictably to the formation of three-dimensional networks. In general, the nominally trigonal topologies of compounds 3a-c favor structures in which hexagonal networks are prominent, so they behave like trimesic acid despite their greater complexity and flexibility. The structures of all crystals incorporate open networks with significant fractions of volume accessible to guests (32-60%). Despite their flexibility, compounds 3a-c appear to be unable to assume conformations that pack efficiently and simultaneously allow the DAT groups to engage in normal hydrogen bonding.

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.

How this classification was reachedexpand

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 categoriesInsufficient payload (model declined to judge)
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 score0.014
Threshold uncertainty score0.997

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 integrity0.0000.000
Insufficient payload (model declined to judge)0.0040.000

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 head0.008
GPT teacher head0.212
Teacher spread0.204 · 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

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations15
Published2016
Admission routes2
Has abstractyes

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