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Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX 2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes
Author(s) -
Ben Aissa Mohamed Ali,
Hassen Sabri,
Arfaoui Youssef
Publication year - 2019
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.25837
Subject(s) - chalcogen , natural bond orbital , lone pair , chemistry , density functional theory , diazine , supramolecular chemistry , pyridazine , crystallography , hydrogen bond , computational chemistry , molecule , non covalent interactions , stereochemistry , crystal structure , organic chemistry
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 CX 2 (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. CTe 2 and CSe 2 form a stronger chalcogen bond than CS 2 . The electrostatic potential of CX 2 (X = S, Se and Te) reveals the presence of two equivalent σ‐holes, one on each chalcogen atom. These CX 2 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.