Quantification of Lewis Acidity and Lewis Basicity: A Density‐Based Reactivity Theory Study
Bibliographic record
Abstract
Lewis acidity and basicity are among the most widely applied concepts across chemistry, biology, and related disciplines. Yet, their accurate calculation and prediction remain challenging. In this study, we employ descriptors derived from density-based reactivity theory to offer a new and quantitative perspective. To this end, we analyzed four series of Lewis acids and bases across two types of reactions. Our results demonstrate that Lewis acidity and basicity can be effectively quantified using a range of global and local descriptors from conceptual density functional theory and an information-theoretic approach in density functional theory. Additionally, various electronic properties, including frontier molecular orbitals, molecular electrostatic potential, natural valence atomic orbital energies, and several types of atomic charges, were identified as robust descriptors. Leveraging these features, we constructed machine-learning models capable of accurately predicting Lewis acidity and basicity. We also uncovered a strong correlation between Lewis acidity/basicity and electrophilicity/nucleophilicity, further bridging these conceptual frameworks. The consistent high correlations obtained across descriptors, coupled with the performance of our machine learning models, confirm that Lewis acidity and Lewis basicity can be quantitatively characterized with high fidelity. This work suggests that density-based frameworks could provide a powerful and novel foundation for understanding the hard and soft acids and bases principle.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.001 | 0.003 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.001 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.001 | 0.002 |
| Open science | 0.001 | 0.001 |
| 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 source (direct Gemma or distilled Codex), 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".