Quantifying Vertical Resonance Energy in Aromatic Systems with Natural Bond Orbitals
Bibliographic record
Abstract
Abstract Natural bond orbitals (NBOs) provide the familiar Lewis type (2c–2e − ) localized description of a molecule. Interactions between nearly filled (2e − π or σ) orbitals and empty (π* or σ*) anti‐bonding orbitals represent delocalization in the system and creates a framework to study stereoelectronic interactions. Here we show that deleting the interactions (NBODel) between π and π* orbitals in aromatic systems and acquiring the energy with the NBO program provides a highly intuitive and quantitative picture of π‐aromaticity that correlates with the well‐established nucleus‐independent chemical shift (NICS) method. This natural bond orbital resonance energy (NBO‐RE) measures the vertical resonance energy (VRE) of aromatic systems without the use of an external reference structure. The NBO‐RE method is applicable to the study of local aromaticity in polycyclic aromatic hydrocarbons (PAHs) and other non‐planar systems.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
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".