ArticleJournal of the American Chemical Society2015
Substituent Effects in CH Hydrogen Bond Interactions: Linear Free Energy Relationships and Influence of Anions.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 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
21 citing papers in PubMed.
- Disrupting the Hofmeister bias in salt liquid-liquid extraction with an arylethynyl bisurea anion receptor.Chemical science · 2024Article
- Solvent effects in anion recognition.Nature reviews. Chemistry · 2024Review
- Structural Landscape of α-Acetamidocinnamic Acid Cocrystals with Bipyridine-Based Coformers: Influence of Crystal Packing on Their Thermal and Photophysical Properties.Crystal growth & design · 2024Article
- Aromatic pentaamide macrocycles bind anions with high affinity for transport across biomembranes.Nature chemistry · 2023Article
- C-H···π interactions disrupt electrostatic interactions between non-aqueous electrolytes to increase solubility.Nature chemistry · 2023Article
- The interplay between hydrogen and halogen bonding: substituent effects and their role in the hydrogen bond enhanced halogen bond.Chemical science · 2023Article
- Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.Chemical reviews · 2022Review
- C-H⋯S hydrogen bonding interactions.Chemical Society reviews · 2022Review
- Deuterium equilibrium isotope effects in a supramolecular receptor for the hydrochalcogenide and halide anions.RSC advances · 2021Article
- Anion binding properties of a hollow PdL-cage.Chemical communications (Cambridge, England) · 2021Article
- Solvent-Dependent Linear Free-Energy Relationship in a Flexible Host-Guest System.The Journal of organic chemistry · 2020Article
- Tuning Supramolecular Selectivity for Hydrosulfide: Linear Free Energy Relationships Reveal Preferential C-H Hydrogen Bond Interactions.Journal of the American Chemical Society · 2020Article
- The road to aryl CHanion binding was paved with good intentions: fundamental studies, host design, and historical perspectives in CH hydrogen bonding.Chemical communications (Cambridge, England) · 2019Article
- Bottom-Up Self-Assembled Supramolecular Structures Built by STM at the Solid/Liquid Interface.Materials (Basel, Switzerland) · 2019Article
- Expanding reversible chalcogenide binding: supramolecular receptors for the hydroselenide (HSeChemical science · 2019Article
- Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions.Scientific reports · 2017Article
- Do CH-Anion and Anion-π Interactions Alter the Mechanism of 2:1 Host-Guest Complexation in Arylethynyl Monourea Anion Receptors?Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Computational and Experimental Evidence of Emergent Equilibrium Isotope Effects in Anion Receptor Complexes.Journal of the American Chemical Society · 2017Article
- Anion Recognition as a Supramolecular Switch of Cell Internalization.Journal of the American Chemical Society · 2017Article
- A Synthetic Supramolecular Receptor for the Hydrosulfide Anion.Angewandte Chemie (International ed. in English) · 2016Article
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Authors and funding
7 authors.
Funding
Abstract
Aryl CH hydrogen bonds (HBs) are now commonly recognized as important factors in a number of fields, including molecular biology, stereoselective catalysis, and anion supramolecular chemistry. As the utility of CH HBs has grown, so to has the need to understand the structure-activity relationship for tuning both their strength and selectivity. Although there has been significant computational effort in this area, an experimental study of the substituent effects on CH HBs has not been previously undertaken. Herein we disclose a systematic study of a single CH HB by using traditional urea donors as directing groups in a supramolecular binding cavity. Experimentally determined association constants are examined by a combination of computational (electrostatic potential) and empirical (σm and σp) values for substituent effects. The dominance of electrostatic parameters, as observed in a computational DFT study, is consistent with current CH HB theory; however, a novel anion dependence of the substituent effects is revealed in solution.
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