ArticleJournal of molecular modeling2026
σ-Hole mechanism in chalcogen-bond catalyzed aza-Diels-Alder reaction.
Article in Journal of molecular modeling, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
0 citing papers in PubMed.
No citing paper in PubMed yet.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
Abstract
contextChalcogen bonding (ChB) catalysis has emerged as a promising non-covalent strategy for activating substrates in cycloaddition reactions, yet its mechanistic details in aza‑Diels-Alder transformations remain underexplored. This study systematically investigates the catalytic role of a homologous series of bis(pentafluorophenyl) chalcogenides, (C₆F₅)₂Ch (Ch = S, Se, Te), in the model aza‑Diels-Alder reaction between formaldehyde imine and 1,3‑butadiene. We demonstrate that catalytic activity increases in the order Te > Se > S, directly correlating with the σ‑hole electrophilicity of the chalcogen atom. The catalysts promote reaction asynchronicity by stabilizing the imine LUMO and selectively polarizing its π‑system, thereby lowering the activation barrier through enhanced charge transfer from the diene. Energy decomposition analysis reveals an evolution in the ChB character from dispersion‑dominated (S) to electrostatically driven (Te), rationalizing the observed trend. The catalytic hierarchy persists across solvents of varying polarity, confirming the robustness of this activation mode in solution.
methodsAll calculations were performed using Gaussian 09 software. Geometries of stationary points along the reaction pathway were optimized, and vibrational frequencies were computed at the M06‑2X/aug‑cc‑pVDZ level of theory. Intrinsic reaction coordinate (IRC) calculations verified transition‑state connectivity. Solvent effects were incorporated via the SMD continuum model for n‑heptane, THF, DMSO, and water. Molecular electrostatic potentials were analyzed on the 0.001 a.u. electron‑density isosurface using Multiwfn and VMD. Bonding characteristics were examined using Bader's quantum theory of atoms in molecules (AIM) and the non‑covalent interaction (NCI) index via Multiwfn. Natural bond orbital (NBO) analysis was carried out with NBO 5.0, and energy decomposition analysis (EDA) was employed to quantify interaction energy components.
Indexed as
Identifiers
41843005What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.