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Record W1978990534 · doi:10.1021/jo991833e

Theoretical Calculation of Ionization Potentials for Disubstituted Benzenes:  Additivity vs Non-Additivity of Substituent Effects

2000· article· en· W1978990534 on OpenAlex
Gino A. DiLabio, Derek A. Pratt, James S. Wright

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

VenueThe Journal of Organic Chemistry · 2000
Typearticle
Languageen
FieldPhysics and Astronomy
TopicAdvanced Chemical Physics Studies
Canadian institutionsCarleton University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryAdditive functionIonizationSubstituentComputational chemistryBenzeneIonization energyBenzene derivativesInterpretation (philosophy)Binary numberBasis setDensity functional theoryMedicinal chemistryOrganic chemistryChemical synthesisIon

Abstract

fetched live from OpenAlex

The ionization potentials of 55 para- and 55 meta-disubstituted benzenes, consisting of all binary combinations of electron-withdrawing groups (-NO2, -CF3, -CHO, -COOH) and electron-donating groups (-Cl, -CH3, -OH, -OCH3, -NH2, and -N(CH3)2) have been calculated using density functional theory with the B3LYP functional and a 6-31G(d) basis set. Relative ionization potentials (delta IP), referred to benzene, are compared with experimental values and shown to be in good agreement. The disubstituted data were correlated with monosubstituted delta IP data and shown to require quadratic terms in order to achieve a good fit; the validity of this conclusion was possible due to the low scatter in the calculated data. A simple MO analysis gives a semiquantitative interpretation of the observed trends in substitutent effects, including a discussion of combinations of substituents for which nonadditivity should be expected.

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 score0.050
Threshold uncertainty score0.764

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)0.0010.000

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 head0.003
GPT teacher head0.223
Teacher spread0.220 · 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