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Record W2321189569 · doi:10.1021/cg500726v

Molecular Networks Created by Charge-Assisted Hydrogen Bonding in Phosphonate, Phosphate, and Sulfonate Salts of Bis(amidines)

2014· article· en· W2321189569 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.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueCrystal Growth & Design · 2014
Typearticle
Languageen
FieldEnvironmental Science
TopicChemical Synthesis and Characterization
Canadian institutionsUniversité de Montréal
FundersNatural Sciences and Engineering Research Council of CanadaCanada Research Chairs
KeywordsDicationChemistryPhosphonateHydrogen bondSulfonateSalt (chemistry)AmidinePhosphoric acidInorganic chemistryIonic bondingMetaphosphateMedicinal chemistrySulfonic acidPolymer chemistryIonCrystallographyMoleculePhosphateOrganic chemistry

Abstract

fetched live from OpenAlex

Two bis(amidines), 2,2′-bi-2-imidazoline (BI) and fluoflavin (FF), were treated with phosphonic, phosphoric, and sulfonic acids in an effort to produce crystalline salts composed of ions linked by networks of charge-assisted hydrogen bonds. As intended, mixing bis(amidine) BI with 1,4-benzenediphosphonic acid and 1,3,5-benzenetriphosphonic acid yielded crystals of phosphonate salts of dication H 2 BI +2 . Structural analyses showed that such salts tend to incorporate tapes composed of alternating dications and anions linked by multiple charge-assisted N–H···O hydrogen bonds of type R 2 2 (9) and R 2 1 (7). Typically, the ionic tapes are further connected to form sheets or other assemblies by additional O–H···O hydrogen bonds involving phosphonate anions. An analogous reaction of the more weakly basic bis(amidine) FF with 1,4-benzenedisulfonic acid yielded only a sulfonate salt of monocation HFF +; however, diprotonation could be achieved by phosphoric acid to produce a crystalline salt built from stacks of H 2 FF +2 dications linked to phosphate anions by charge-assisted N–H···O hydrogen bonds of type R 2 2 (8). Together, these results demonstrate that acids with multiple PO(OH) 2 and SO 2 OH groups can react with bis(amidines) to produce salts with structural features resulting predictably from the geometry of the ions and their ability to engage in multiple charge-assisted hydrogen bonds according to standard patterns.

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 categoriesnone
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 score0.029
Threshold uncertainty score0.815

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)0.0000.000

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 head0.006
GPT teacher head0.180
Teacher spread0.174 · 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