ArticleJournal of chemical information and modeling2014
Heteroaromatic π-stacking energy landscapes.
Article in Journal of chemical information and modeling, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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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.
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Who cites it
56 citing papers in PubMed.
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- The catalytic enantioselective [1,2]-Wittig rearrangement cascade of allylic ethers.Nature chemistry · 2026Article
- A Robust Ensemble Machine Learning Approach for Inhibitor Discovery: Case Study of HIV-1 NNRTI and Validation Using MD Simulation.Chemistry, an Asian journal · 2026Article
- Quantum Chemistry in Drug Design: Applications, Challenges, and the Need for Speed.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Making Sense of Heteroatom Effects in π-π Interactions.Journal of the American Chemical Society · 2025Article
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- Target-Guided Design and Synthesis of Aryl-Functionalized Promysalin Analogs.Chembiochem : a European journal of chemical biology · 2025Article
- Stacking Interactions of Druglike Heterocycles with Nucleobases.Journal of chemical information and modeling · 2025Article
- Structural basis of SARS-CoV-2 polymerase inhibition by nonnucleoside inhibitor HeE1-2Tyr.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Molecular Details of Polyester Decrystallization via Molecular Simulation.Macromolecules · 2025Article
- Synthesis and crystal structure of 2,2,2-tri-chloroethylActa crystallographica. Section E, Crystallographic communications · 2025Article
- London dispersion forces and steric effects within nanocomposites tune interaction energies and chain conformation.Communications chemistry · 2025Article
- Evaluation of expanded 2-aminobenzothiazole library as inhibitors of a model histidine kinase and virulence suppressors in Pseudomonas aeruginosa.Bioorganic chemistry · 2024Article
- Catching the π-Stacks: Prediction of Aggregate Structures of Porphyrin.The journal of physical chemistry. A · 2024Article
- Photoswitchable positive allosteric modulators of metabotropic glutamate receptor 4 to improve selectivity.iScience · 2024Article
- A Naphthoquinoline-Dione-Based CuMolecules (Basel, Switzerland) · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In this study we investigate π-stacking interactions of a variety of aromatic heterocycles with benzene using dispersion corrected density functional theory. We calculate extensive potential energy surfaces for parallel-displaced interaction geometries. We find that dispersion contributes significantly to the interaction energy and is complemented by a varying degree of electrostatic interactions. We identify geometric preferences and minimum interaction energies for a set of 13 5- and 6-membered aromatic heterocycles frequently encountered in small drug-like molecules. We demonstrate that the electrostatic properties of these systems are a key determinant for their orientational preferences. The results of this study can be applied in lead optimization for the improvement of stacking interactions, as it provides detailed energy landscapes for a wide range of coplanar heteroaromatic geometries. These energy landscapes can serve as a guide for ring replacement in structure-based drug design.
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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.