Abstract
Pyrylium salts are a very important class of organic molecules containing a trivalent oxygen atom in a six-membered aromatic ring. In this manuscript, we report a theoretical study of pyrylium salts and their thio-, seleno- and telluro- analogues by means of DFT calculations. For this purpose, unsubstituted 2,4,6-trimethyl and 2,4,6-triphenyl cations and anions with different morphologies were chosen (Cl–, NO3– and BF4–). The complexes were characterized by means of natural bond orbital and “atoms-in-molecules” theories, and the physical nature of the interactions has been analyzed by means of symmetry-adapted perturbation theory calculations. Our results indicate the presence of anion-π interactions and chalcogen bonds based on both σ- and π-hole interactions and the existence of very favorable σ-complexes, especially for unsubstituted cations. The electrostatic component is dominant in the interactions, although the induction contributions are important, particularly for chloride complexes. The geometrical features of the complexes have been compared with experimental data retrieved from the Cambridge Structural Database.
Highlights
Noncovalent interactions have a constitutive role in the science of intermolecular relationships.In particular, those involving aromatic rings play a vital role in chemistry and biology [1], whichMolecules 2015, 20 becomes prominent in drug-receptor interactions, crystal engineering and protein folding [2]
We chose different aromatic systems to interact with chloride, namely pyrylium, thiopyrylium and selenopyrylium (1, 2 and 3, respectively, in Scheme 1)
We carried out Density Functional Theory (DFT)
Summary
Noncovalent interactions have a constitutive role in the science of intermolecular relationships.In particular, those involving aromatic rings play a vital role in chemistry and biology [1], whichMolecules 2015, 20 becomes prominent in drug-receptor interactions, crystal engineering and protein folding [2]. The contact between an anion and the region above the plane of an electron-deficient aromatic ring has been recognized as a noncovalent bonding interaction. Pyrylium salts are a very important class of cationic organic molecules containing a trivalent oxygen atom in a six-membered aromatic ring [20,21]. They can act as intermediates for a variety of syntheses [22]
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