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Record W2017644087 · doi:10.1021/jo051823f

Solvent Effect on the α-Effect:  Ground-State versus Transition-State Effects; a Combined Calorimetric and Kinetic Investigation

2006· article· en· W2017644087 on OpenAlexaff
Ik‐Hwan Um, So-Jeong Hwang, Erwin Buncel

Bibliographic record

VenueThe Journal of Organic Chemistry · 2006
Typearticle
Languageen
FieldPhysics and Astronomy
TopicSpectroscopy and Quantum Chemical Studies
Canadian institutionsQueen's University
Fundersnot available
KeywordsChemistrySolvationNucleophileGround stateDimethyl sulfoxideSolventSolvent effectsReaction rate constantKineticsComputational chemistryPhotochemistryOrganic chemistryCatalysisAtomic physics

Abstract

fetched live from OpenAlex

In a study of the solvent effect on the alpha-effect, second-order rate constants (kNu-) have been determined spectrophotometrically for reactions of a series of substituted phenyl acetates with butan-2,3-dione monoximate (Ox-, alpha-nucleophile) and p-chlorophenoxide (p-ClPhO-, reference nucleophile) in DMSO-H2O (DMSO = dimethyl sulfoxide) mixtures of varying compositions at 25.0 +/- 0.1 degrees C. The magnitude of the alpha-effect, kOx-/kp-ClPhO-, increases as the DMSO content in the medium increases up to 40-50 mol %, reaching 500, one of the largest alpha-effect values, and then decreases on further addition of DMSO, resulting in a bell-shaped alpha-effect profile regardless of the nature of the substrates. The magnitude of the alpha-effect is found to be significantly dependent on the substrates (or, more quantitatively, on beta(nuc)). Thus, beta(nuc) is an important predictor of the magnitude of the alpha-effect. The bell-shaped alpha-effect profile found in the present system is attributed to the differential change in the sensitivity of the medium effect on the Ox- and p-ClPhO- systems but not due to a change in the reaction mechanism or to a drastic change in the basicity of the two nucleophiles on addition of DMSO to the medium. Through application of calorimetric measurements of ground-state solvation combined with the diagnostic beta(nuc) values, it is shown that the transition-state effect is more dominant than the ground-state effect as the origin of the alpha-effect in the present system.

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)0.000
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 score0.006
Threshold uncertainty score0.418

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 head0.005
GPT teacher head0.206
Teacher spread0.201 · 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.

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

Citations45
Published2006
Admission routes1
Has abstractyes

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