ArticlePhysical chemistry chemical physics : PCCP2015
Cation-π interactions: computational analyses of the aromatic box motif and the fluorination strategy for experimental evaluation.
Article in Physical chemistry chemical physics : PCCP, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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37 citing papers in PubMed.
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- Attractive Noncovalent Interactions versus Steric Confinement in Asymmetric Supramolecular Catalysis.Journal of the American Chemical Society · 2026Article
- Hidden Interactions: Quantum Perspectives in Drug Design.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Investigating the Site-Specific Impact of Fluorine Substitution on Aromatic Interactions in a Tryptophan Zipper Peptide.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Cryo-EM structures of the small-conductance CaNature communications · 2025Article
- A Disila[2]ferrocenophane with a Bridging 9,9'-Bi-9Molecules (Basel, Switzerland) · 2025Article
- The Cation-π Interaction in Chemistry and Biology.Chemical reviews · 2025Review
- Anion-Facilitated Hydrogen-Deuterium Exchange as a Tool to Probe Weak Anion-Protein Interactions Responsible for Hofmeister Effects.The journal of physical chemistry. B · 2025Article
- Molecular Insights into the Adsorption of Deposit Control Additives from Hydrocarbon Fuels.Langmuir : the ACS journal of surfaces and colloids · 2025Article
- Solvent Effect on Cation⊗3π Interactions: A First-Principles Study.Molecules (Basel, Switzerland) · 2024Article
- Genetic Code Expansion for Mechanistic Studies in Ion Channels: An (Un)natural Union of Chemistry and Biology.Chemical reviews · 2024Review
- α-Aminophosphonate inhibitors of metallo-β-lactamases NDM-1 and VIM-2.RSC medicinal chemistry · 2023Article
- Tryptophan Stabilization of a Biochemical Carbocation Evaluated by Analysis of π Complexes of 3-Ethylindole with theACS omega · 2023Article
- Tuning phenylalanine fluorination to assess aromatic contributions to protein function and stability in cells.Nature communications · 2023Article
- Electrostatic Contributions to the Binding Free Energy of Nicotine to the Acetylcholine Binding Protein.The journal of physical chemistry. B · 2022Article
- Structure and mechanism for iterative amideProceedings of the National Academy of Sciences of the United States of America · 2022Article
- Comparative Analysis of Sulfonium-π, Ammonium-π, and Sulfur-π Interactions and Relevance to SAM-Dependent Methyltransferases.Journal of the American Chemical Society · 2022Article
- Structural and catalytic characterization of Blastochloris viridis and Pseudomonas aeruginosa homospermidine synthases supports the essential role of cation-π interaction.Acta crystallographica. Section D, Structural biology · 2021Article
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Abstract
Cation-π interactions are common in biological systems, and many structural studies have revealed the aromatic box as a common motif. With the aim of understanding the nature of the aromatic box, several computational methods were evaluated for their ability to reproduce experimental cation-π binding energies. We find the DFT method M06 with the 6-31G(d,p) basis set performs best of several methods tested. The binding of benzene to a number of different cations (sodium, potassium, ammonium, tetramethylammonium, and guanidinium) was studied. In addition, the binding of the organic cations NH4(+) and NMe4(+) to ab initio generated aromatic boxes as well as examples of aromatic boxes from protein crystal structures were investigated. These data, along with a study of the distance dependence of the cation-π interaction, indicate that multiple aromatic residues can meaningfully contribute to cation binding, even with displacements of more than an angstrom from the optimal cation-π interaction. Progressive fluorination of benzene and indole was studied as well, and binding energies obtained were used to reaffirm the validity of the "fluorination strategy" to study cation-π interactions in vivo.
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