Anion‐π Interaction for Molecular Recognition of Anions: Focus on Cooperativity with Hydrogen Bonding

Abstract

Anion recognition represents an intense area of research in supramolecular chemistry. The last two decades have been marked by spectacular advances in the design of new anion receptors. Moreover, the development of approaches combining Jean-Yves Salpin got his PhD in chemistry from the University of Orsay in 1997. Then, from 1997 and 1999, he held postdoctoral positions at the University of Bielefeld (Germany) and at the Catholic University of Leuven (Belgium). Back in France, he works since 1999 as a full research scientist at the Centre National pour la Recherche Scientifique (CNRS). His research interests lie in the field of gas-phase ion chemistry by combining mass spectrometry and quantum chemistry. Promoted CNRS senior research scientist in 2012, his major field of research concerns the reactivity of metal ions (alkalineearth, transition metal, heavy metals) towards organic molecules or biomolecules, and more recently the study of interactions of both anionic and cationic receptors.

Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pimpinella anisum L. Seeds), Esculetin, and 4-Methyl-Esculetin Using X-ray Diffraction, Hydrodynamic Voltammetry and DFT Methods

“…[ 12 , 29 , 31 ]. Frequently, as in the case of the two coumarins described in our study, hydrogen bonding acts in a cooperative manner to stabilize the intermolecular interactions [ 39 ]. Description of the nature of anion– π interactions is still much discussed in the literature [ 40 , 41 , 42 ].…”

Tetrafluoroterephthalonitrile as an anion‐π donor: theoretical evaluation and application to anion recognition

“…Furthermore, the symmetric architecture and 1,4‐bis‐substitution pattern of s ‐tetrazine derivatives tend to form receptor‐anion complexes with a preferential η 6 coordination mode [12] . Therefore, moving from tetrazine derivatives to new anion‐π‐acidic arenes [10] will allow gaining insights into the relationship between fragments and rationalizing binding events for a better understanding of the associated recognition phenomena and fine structure‐properties relationships.…”

“…Moreover, the combination of several different weak interactions within a single receptor has aroused the growing curiosity of supramolecular chemists over the past twenty years [9] . The exploration of binding properties of receptors combining both H‐bond donor and anion‐π donor fragments is an emerging trend depending on the nature of the two fragments involved and the topology of the receptor [10] . As an example, within the same family of receptors combining urea and tetrazine derivatives, cooperative or anti ‐cooperative effects on chloride binding events have recently been observed [10–13] .…”

“…The exploration of binding properties of receptors combining both H‐bond donor and anion‐π donor fragments is an emerging trend depending on the nature of the two fragments involved and the topology of the receptor [10] . As an example, within the same family of receptors combining urea and tetrazine derivatives, cooperative or anti ‐cooperative effects on chloride binding events have recently been observed [10–13] . Furthermore, the symmetric architecture and 1,4‐bis‐substitution pattern of s ‐tetrazine derivatives tend to form receptor‐anion complexes with a preferential η 6 coordination mode [12] .…”

Symmetry of Hydrogen Bonds: Application of NMR Method of Isotopic Perturbation and Relevance of Solvatomers

“…Hydrogen bonding is a key feature of molecular structure and energetics [1,2]. It is key to understanding the structure and properties of water, proteins, and DNA, and it is currently of interest for understanding systems that exhibit molecular recognition [3].…”