Next Article in Journal
Friedelin in Maytenus ilicifolia Is Produced by Friedelin Synthase Isoforms
Next Article in Special Issue
Understanding the Molecule-Electrode Interface for Molecular Spintronic Devices: A Computational and Experimental Study
Previous Article in Journal
Structure-Based Discovery of a Series of 5H-Pyrrolo[2,3-b]pyrazine FGFR Kinase Inhibitors
Previous Article in Special Issue
Network Formation via Anion Coordination: Crystal Structures Based on the Interplay of Non-Covalent Interactions
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(3), 699; https://doi.org/10.3390/molecules23030699

Chalcogen ‘like-like’ Interactions Involving Trisulphide and Triselenide Compounds: A Combined CSD and Ab Initio Study

Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
*
Authors to whom correspondence should be addressed.
Received: 5 March 2018 / Revised: 15 March 2018 / Accepted: 15 March 2018 / Published: 19 March 2018
(This article belongs to the Special Issue Noncovalent Interactions: A Useful Tool for Crystal Design)
Full-Text   |   PDF [2705 KB, uploaded 3 May 2018]   |  

Abstract

In this manuscript, we combined a search in the Cambridge Structural Database (CSD) and ab initio calculations (RI-MP2/def2-TZVPD level of theory) to analyze the ability of trisulphide and triselenide moieties to establish chalcogen ‘like-like’ interactions. A preliminary CSD inspection revealed two predominant structural patterns, depending on the anti or syn conformation adopted by the substituents of the S3/Se3 bridge, leading to bifurcated or double chalcogen bonding interactions, respectively. In order to analyze these two relevant structural motifs we have used a series of S and Se derivatives Ch3X2 (Ch = S and Se and X = H, F, CN, and CF3) which act as both electron donor (using the lone pairs) and acceptor (using the σ-holes) entities. Besides, we have carried out “atoms in molecules” (AIM) and natural bonding orbital (NBO) analyses to further describe and characterize the chalcogen bonding interactions described herein. As far as we know, chalcogen···chalcogen interactions involving trichalconides (S3/Se3) have not been previously described in literature a may be of great importance in the preparation and characterization of new solids based on this subclass of σ-hole bonding. View Full-Text
Keywords: chalcogen bonding interactions; CSD search; RI-MP2 calculations; AIM and NBO analyses chalcogen bonding interactions; CSD search; RI-MP2 calculations; AIM and NBO analyses
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Bauzá, A.; Frontera, A. Chalcogen ‘like-like’ Interactions Involving Trisulphide and Triselenide Compounds: A Combined CSD and Ab Initio Study. Molecules 2018, 23, 699.

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.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top