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Record W4385500896 · doi:10.1039/d3cc03229a

Mechanism to model: a physical organic chemistry approach to reaction prediction

2023· review· en· W4385500896 on OpenAlexafffund
Jolene P. Reid, Isaiah O. Betinol, Yutao Kuang

Bibliographic record

VenueChemical Communications · 2023
Typereview
Languageen
FieldChemistry
TopicAsymmetric Synthesis and Catalysis
Canadian institutionsUniversity of British Columbia
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsGeneralizationEnantioselective synthesisTransferabilityOrganocatalysisMechanism (biology)Biochemical engineeringComputer scienceChemistryReaction mechanismCatalysisComputational chemistryMachine learningOrganic chemistryMathematicsEpistemology

Abstract

fetched live from OpenAlex

The application of mechanistic generalizations is at the core of chemical reaction development and application. These strategies are rooted in physical organic chemistry where mechanistic understandings can be derived from one reaction and applied to explain another. Over time these techniques have evolved from rationalizing observed outcomes to leading experimental design through reaction prediction. In parallel, significant progression in asymmetric organocatalysis has expanded the reach of chiral transfer to new reactions with increased efficiency. However, the complex and diverse catalyst structures applied in this arena have rendered the generalization of asymmetric catalytic processes to be exceptionally challenging. Recognizing this, a portion of our research has been focused on understanding the transferability of chemical observations between similar reactions and exploiting this phenomenon as a platform for prediction. Through these experiences, we have relied on a working knowledge of reaction mechanism to guide the development and application of our models which have been advanced from simple qualitative rules to large statistical models for quantitative predictions. In this feature article, we describe the models acquired to generalize organocatalytic reaction mechanisms and demonstrate their use as a powerful approach for accelerating enantioselective synthesis.

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Review · Consensus signal: Review
Teacher disagreement score0.961
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0010.001
Bibliometrics0.0000.002
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0030.002
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0000.001

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 head0.102
GPT teacher head0.331
Teacher spread0.229 · 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 designNot applicable
Domainnot available
GenreReview

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

Citations13
Published2023
Admission routes2
Has abstractyes

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