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Theoretical Description of R–X⋯NH3 Halogen Bond Complexes: Effect of the R Group on the Complex Stability and Sigma-Hole Electron Depletion

Anion Recognition by Neutral and Cationic Iodotriazole Halogen Bonding Scaffolds

Trinity Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, D02 R590 Dublin 2, Ireland
Irish Centre of High-End Computing, Grand Canal Quay, Dublin 2, Ireland & School of Chemistry, University College Dublin, Belfield, D02 HP83 Dublin 4, Ireland
Author to whom correspondence should be addressed.
Academic Editor: Paulo Jorge Costa
Molecules 2020, 25(4), 798;
Received: 20 December 2019 / Revised: 7 February 2020 / Accepted: 10 February 2020 / Published: 12 February 2020
(This article belongs to the Special Issue Halogen Bonding: Insights from Computational Tools)
A computational study of the iodide discrimination by different neutral and cationic iodotriazole halogen bonding hosts was carried out by means of Density Functional Theory. The importance of the size of the scaffold was highlighted and its impact observed in the binding energies and intermolecular X⋯I distances. Larger scaffolds were found to reduce the electronic repulsion and increase the overlap between the halide electron lone pair and the corresponding I-C antibonding orbital, increasing the halogen bonding interactions. Additionally, the planarity plays an important role within the interaction, and can be tuned using hydroxyl to perform intramolecular hydrogen bonds (IMHB) between the scaffold and the halogen atoms. Structures with IMHB exhibit stronger halogen bond interactions, as evidenced by the shorter intramolecular distances, larger electron density values at the bond critical point and more negative binding energies. View Full-Text
Keywords: halogen bond; anion recognition; DFT study halogen bond; anion recognition; DFT study
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MDPI and ACS Style

Iribarren, I.; Sánchez-Sanz, G.; Trujillo, C. Anion Recognition by Neutral and Cationic Iodotriazole Halogen Bonding Scaffolds. Molecules 2020, 25, 798.

AMA Style

Iribarren I, Sánchez-Sanz G, Trujillo C. Anion Recognition by Neutral and Cationic Iodotriazole Halogen Bonding Scaffolds. Molecules. 2020; 25(4):798.

Chicago/Turabian Style

Iribarren, Iñigo, Goar Sánchez-Sanz, and Cristina Trujillo. 2020. "Anion Recognition by Neutral and Cationic Iodotriazole Halogen Bonding Scaffolds" Molecules 25, no. 4: 798.

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