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Record W2762684335 · doi:10.1021/jacs.7b09983

Enantioselective Recognition of Ammonium Carbamates in a Chiral Metal–Organic Framework

2017· article· en· W2762684335 on OpenAlexfundno aff
Jeffrey D. Martell, Leo B. Zasada, Alexander C. Forse, Rebecca L. Siegelman, Miguel I. Gonzalez, Julia Oktawiec, Tomče Runčevski, Jiawei Xu, Monika Srebro‐Hooper, Phillip J. Milner, Kristen A. Colwell, Jochen Autschbach, Jeffrey A. Reimer, Jeffrey R. Long

Bibliographic record

VenueJournal of the American Chemical Society · 2017
Typearticle
Languageen
FieldChemistry
TopicMolecular Sensors and Ion Detection
Canadian institutionsnot available
FundersLawrence Berkeley National LaboratoryDivision of ChemistryNational Institute of General Medical SciencesNational Science FoundationUniversity at BuffaloOffice of ScienceAdvanced Research Projects Agency - EnergyMinisterstwo Edukacji i NaukiArgonne National LaboratoryU.S. Department of EnergyPhilomathia FoundationNational Institutes of HealthAdolph C. and Mary Sprague Miller Institute for Basic Research in Science, University of California BerkeleyBasic Energy SciencesUniversity of California BerkeleyAdvanced Research Projects Agency
KeywordsChemistryEnantioselective synthesisAmmoniumCombinatorial chemistryOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Chiral metal–organic frameworks have attracted interest for enantioselective separations and catalysis because of their high crystallinity and pores with tunable shapes, sizes, and chemical environments. Chiral frameworks of the type M 2 (dobpdc) (M = Mg, Mn, Fe, Co, Ni, Zn; dobpdc 4– = 4,4′-dioxidobiphenyl-3,3′-dicarboxylate) seem particularly promising for potential applications because of their excellent stability, high internal surface areas, and strongly polarizing open metal coordination sites within the channels, but to date these materials have been isolated only in racemic form. Here, we demonstrate that when appended with the chiral diamine trans -1,2-diaminocyclohexane (dach), Mg 2 (dobpdc) adsorbs carbon dioxide cooperatively to form ammonium carbamate chains, and the thermodynamics of CO 2 capture are strongly influenced by enantioselective interactions within the chiral pores of the framework. We further show that it is possible to access both enantiomers of Mg 2 (dobpdc) with high enantiopurity (≥90%) via framework synthesis in the presence of varying quantities of d -panthenol, an inexpensive chiral induction agent. Investigation of dach–M 2 (dobpdc) samples following CO 2 adsorption─using single-crystal and powder X-ray diffraction, solid-state nuclear magnetic resonance spectroscopy, and density functional theory calculations─revealed that the ammonium carbamate chains interact extensively with each other and with the chiral M 2 (dobpdc) pore walls. Subtle differences in the non-covalent interactions accessible in each diastereomeric phase dramatically impact the thermodynamics of CO 2 adsorption.

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 score0.002
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

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)0.0010.000

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 head0.011
GPT teacher head0.249
Teacher spread0.238 · 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

Citations104
Published2017
Admission routes1
Has abstractyes

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