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Record W2328419081 · doi:10.1021/ja202096f

Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity With Combinations of Distinct Noncovalent Interactions

2011· article· en· W2328419081 on OpenAlexaff
Michael G. Chudzinski, C.A. McClary, Mark S. Taylor

Bibliographic record

VenueJournal of the American Chemical Society · 2011
Typearticle
Languageen
FieldChemistry
TopicCrystallography and molecular interactions
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryHalogen bondHydrogen bondHalogenNon-covalent interactionsSubstituentHalideFluorineSelectivityBinding energyIonComputational chemistryPhotochemistryMoleculeStereochemistryInorganic chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Studies of a series of urea-based anion receptors designed to probe the potential for anion recognition through combinations of hydrogen and halogen bonding are presented. Proton- and fluorine-NMR spectroscopy indicates that the two interactions act in concert to achieve binding of certain anions, a conclusion supported by computational studies. Replacement of the halogen-bond donating iodine substituent by fluorine (which does not participate in halogen bonding) enables estimation of the contribution of this interaction to the free energy of anion binding. Evidence for attractive contacts between anions and electron-deficient arenes arising from the use of perfluoroarene-functionalized ureas as control receptors is also discussed. The magnitude of the free energy contribution of halogen bonding depends both on the geometric features of the group linking the hydrogen- and halogen-bond donor groups and on the identity of the bound anion. The results are interpreted in relation to fundamental features of the halogen-bonding interaction, including its directionality and unusual preference for halides over oxoanions. Cooperation between two distinct noncovalent interactions leads to unusual effects on receptor selectivity, a result of fundamental differences in the interactions of halogen- and hydrogen-bond donor groups with anions.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.001
Threshold uncertainty score0.003

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0010.000

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 head0.012
GPT teacher head0.237
Teacher spread0.225 · 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 source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations288
Published2011
Admission routes1
Has abstractyes

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Same venueJournal of the American Chemical SocietySame topicCrystallography and molecular interactionsFrench-language works237,207