Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes

Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) a...

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Bibliographic Details
Published in:International journal of quantum chemistry 2019-03, Vol.119 (6), p.n/a
Main Authors: Ben Aissa, Mohamed Ali, Hassen, Sabri, Arfaoui, Youssef
Format: Article
Language:English
Subjects:
Aromatic compounds
Chalcogen bonds
chalcogen‐bonding
Chemistry
Density functional theory
Hydrogen bonding
noncovalent interaction
Perturbation methods
Perturbation theory
Physical chemistry
Quantum physics
supramolecular complexes
Tellurium
Theoretical density
Theory
σ‐hole
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Summary:Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) and diazine (pyridazine, pyrimidine and pyrazine). Chalcogen atoms prefer interacting with the lone pair of a nitrogen atom rather than with the π‐cloud of an aromatic ring. CTe2 and CSe2 form a stronger chalcogen bond than CS2. The electrostatic potential of CX2 (X = S, Se and Te) reveals the presence of two equivalent σ‐holes, one on each chalcogen atom. These CX2 molecules interact with diazine giving rise to supramolecular interactions. Wiberg bond index and second‐order perturbation theory analysis in NBO were performed to better understand the nature of the chalcogen bond interaction. Formation of supramolecular assemblies by charge transfer interactions between an aromatic heterocyclic such as Lewis base compounds containing nitrogen atom and an electrophilic region of a chalcogen (S, Se and Te). These interactions can play a dominant role in the fields of supramolecular architecture, molecular recognition, materials science and crystal engineering.
ISSN:0020-7608
1097-461X
DOI:10.1002/qua.25837