@article {175, title = {Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis}, journal = {Chemistry {\textendash} A European Journal}, volume = {27}, year = {2021}, month = {2020/11/19}, pages = {2315{\textendash}2320}, abstract = {

Halogen bonding represents a powerful tool in the field of noncovalent interactions. However, applications in enantioselective recognition and catalysis remain almost nonexistent, due in part to the distinct features of halogen bonds, including long covalent and noncovalent bond distances and high directionality. Herein, we present a novel chiral tetrakis-iodo-triazole structure as a neutral halogen bond donor for both chiral anion-recognition and enantioinduction in ion-pair organocatalysis. NMR-titration studies revealed significant differences in anion affinity between the halogen bonding receptor and its hydrogen bonding parent. Selective recognition of chiral dicarboxylates and asymmetric induction in a benchmark organocatalytic reaction were demonstrated using the halogen bond donor. Inversions in the absolute sense of chiral recognition, enantioselectivity, and chiroptical properties relative to the related hydrogen donor were observed. Computational modeling suggested that these effects were the result of distinct anion-binding modes for the halogen- versus hydrogen-bond donors.

}, keywords = {Chiral anion recognition, DFT, Halogen bonding, NMR-titration, organocatalysis}, isbn = {0947-6539}, url = {https://doi.org/10.1002/chem.202005016}, author = {Ostler, Florian and Piekarski, Dariusz G. and Danelzik, Tobias and Taylor, Mark and Garc{\'\i}a Manche{\~n}o, Olga} } @article {168, title = {Anion recognition based on halogen, chalcogen, pnictogen and tetrel bonding}, journal = {Coordination Chemistry Reviews}, volume = {413}, year = {2020}, month = {2020/06/15/}, pages = {213270}, abstract = {

Compounds incorporating Group 14{\textendash}17 elements as electron-deficient sites are capable of attractive, directional interactions with Lewis bases. These noncovalent interactions are known as tetrel, pnictogen, chalcogen and halogen bonding, respectively. When the Lewis base is a negatively charged species, such interactions can be employed as the basis for the development of anion receptors, which are of interest from a fundamental standpoint and in applications ranging from chemical sensing to catalysis and medicinal chemistry. Halogen bonding and related interactions offer intriguing features in this context, including distinctive patterns of anion selectivity and solvent effects, along with unique opportunities for structural variation and synthetic access. This review article summarizes advances in anion recognition using halogen, chalcogen, pnictogen and tetrel bonding, with a focus on examples for which solution-phase thermodynamic data have been obtained.

}, keywords = {Anion recognition, Chalcogen bonding, Halogen bonding, noncovalent interactions, Pnictogen bonding, supramolecular chemistry, Tetrel bonding}, isbn = {0010-8545}, url = {http://www.sciencedirect.com/science/article/pii/S0010854519307805}, author = {Taylor, Mark S.} } @inbook {112, title = {Halogen Bond-Based Receptors}, booktitle = {Reference Module in Chemistry, Molecular Sciences and Chemical Engineering}, year = {2016}, pages = { - }, publisher = {Elsevier}, organization = {Elsevier}, abstract = {

AbstractThis article presents an overview of applications of halogen bonding in host{\textendash}guest chemistry and molecular recognition. Halogen bonds are attractive interactions between covalently bonded, electron-deficient halogens and Lewis bases. In recent years, it has become increasingly evident that halogen bonding interactions of organic donors (i.e., compounds having C{\textendash}X bonds) can have appreciable strength and pronounced directionality in solution. In a relatively short period of time, impressive progress has been made in using halogen bonding as a design feature for the construction of supramolecular systems such as anion receptors and transporters, chemical sensors, molecular capsules, and mechanically interlocked molecules. Not only can halogen bonds act as {\textquotedblleft}replacements{\textquotedblright} for the hydrogen bonds that are conventionally employed in such contexts, but also they can give rise to unique properties and behaviors due to differences between the two types of interactions.

}, keywords = {Anion recognition, Halogen bonding, Mechanically interlocked molecules, Molecular encapsulation, supramolecular chemistry}, isbn = {978-0-12-409547-2}, url = {http://www.sciencedirect.com/science/article/pii/B9780124095472125272}, author = {Taylor, M.S.} }