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Record W2023476524 · doi:10.1002/poc.763

Reactions of carbocations with water and azide ion: calculation of rate constants from equilibrium constants and distortion energies using No Barrier Theory

2004· article· en· W2023476524 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

VenueJournal of Physical Organic Chemistry · 2004
Typearticle
Languageen
FieldChemistry
TopicChemical Reaction Mechanisms
Canadian institutionsWestern University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryReaction rate constantAzideEquilibrium constantCarbocationSolvationPhysical chemistryComputational chemistryThermodynamicsIonPhotochemistryOrganic chemistryKinetics

Abstract

fetched live from OpenAlex

Abstract Rate constants for the reaction of water or azide ion with various substituted benzylic carbocations can be calculated from the equilibrium constants for cation formation and distortion energies by means of the No Barrier Theory. Rate constants for the water reactions span 10 orders of magnitude. Most but not all of the azide reactions are diffusion controlled. The rate constants, and in particular those less than diffusion controlled, were successfully calculated. The set of equilibrium constants available from the literature was supplemented using alkyl chloride hydrolysis equilibrium constants and relative cation formation equilibrium constants derived from DFT/continuum calculations. The model used for these reactions allows for the entropic cost of bringing solutes together, the desolvational cost of losing hydrogen bonding solvation by water and the cost of moving the aryl ring through the solvent as the central atom changes from sp 2 to sp 3 hybridization and from planar to pyramidal geometry. Copyright © 2004 John Wiley & Sons, Ltd.

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 score0.004
Threshold uncertainty score0.514

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 head0.007
GPT teacher head0.224
Teacher spread0.216 · 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