Next Article in Journal
Pterostilbene and 4′-Methoxyresveratrol Inhibited Lipopolysaccharide-Induced Inflammatory Response in RAW264.7 Macrophages
Next Article in Special Issue
Tetrel Bonds with π-Electrons Acting as Lewis Bases—Theoretical Results and Experimental Evidences
Previous Article in Journal
Effect of Microwave Vacuum Drying on the Drying Characteristics, Color, Microstructure, and Antioxidant Activity of Green Coffee Beans
Previous Article in Special Issue
Complexes of CO2 with the Azoles: Tetrel Bonds, Hydrogen Bonds and Other Secondary Interactions
Open AccessFeature PaperArticle

Tetrel Bonding as a Vehicle for Strong and Selective Anion Binding

Department of Chemistry and Biochemistry, Utah State University, Logan, UT 84322-0300, USA
Molecules 2018, 23(5), 1147; https://doi.org/10.3390/molecules23051147
Received: 24 April 2018 / Revised: 7 May 2018 / Accepted: 9 May 2018 / Published: 11 May 2018
(This article belongs to the Special Issue Tetrel Bonds)
Tetrel atoms T (T = Si, Ge, Sn, and Pb) can engage in very strong noncovalent interactions with nucleophiles, which are commonly referred to as tetrel bonds. The ability of such bonds to bind various anions is assessed with a goal of designing an optimal receptor. The Sn atom seems to form the strongest bonds within the tetrel family. It is most effective in the context of a -SnF3 group and a further enhancement is observed when a positive charge is placed on the receptor. Connection of the -SnF3 group to either an imidazolium or triazolium provides a strong halide receptor, which can be improved if its point of attachment is changed from the C to an N atom of either ring. Aromaticity of the ring offers no advantage nor is a cyclic system superior to a simple alkyl amine of any chain length. Placing a pair of -SnF3 groups on a single molecule to form a bipodal dicationic receptor with two tetrel bonds enhances the binding, but falls short of a simple doubling. These two tetrel groups can be placed on opposite ends of an alkyl diamine chain of any length although SnF3+NH2(CH2)nNH2SnF3+ with n between 2 and 4 seems to offer the strongest halide binding. Of the various anions tested, OH binds most strongly: OH > F > Cl > Br > I. The binding energy of the larger NO3 and HCO3 anions is more dependent upon the charge of the receptor. This pattern translates into very strong selectivity of binding one anion over another. The tetrel-bonding receptors bind far more strongly to each anion than an equivalent number of K+ counterions, which leads to equilibrium ratios in favor of the former of many orders of magnitude. View Full-Text
Keywords: bipodal; Gibbs free energy; imidazolium; triazolium; counterion; deformation energy bipodal; Gibbs free energy; imidazolium; triazolium; counterion; deformation energy
Show Figures

Graphical abstract

MDPI and ACS Style

Scheiner, S. Tetrel Bonding as a Vehicle for Strong and Selective Anion Binding. Molecules 2018, 23, 1147.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop