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Computational studies on the conformational preference of N ‐(Thiazol‐2‐yl) benzamide
Author(s) -
Zonouzi Afsaneh,
Kakeshpour Ali,
Ranjbar Parviz Rashidi,
Moradi Ashraf
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201900277
Subject(s) - natural bond orbital , chemistry , intramolecular force , conformational isomerism , hydrogen bond , crystallography , atoms in molecules , van der waals force , van der waals radius , stereochemistry , molecule , non covalent interactions , computational chemistry , benzamide , amide , density functional theory , organic chemistry
Abstract N ‐(Thiazol‐2‐yl) benzamide 1 substructures are found in some of bioactive compounds. In some of protein/ligand co‐crystals, the 1 moiety adopts a conformer in which the amide O and the thiazole S atoms are close. In fact, in the crystalline structure of 1 , the O—S distance is even shorter than Van der Waals radius. Although the natural bond orbital analysis finds a weak stabilizing interaction between O and S atoms, the attractive dipole–dipole interaction between the amide N─H and thiazole N atom seems to play a more significant role. Moreover, an intramolecular O—H hydrogen bonding in dimeric forms found to have an important role in the conformation preference of 1 . Computational details for the stability of conformers have been discussed using quantum theory of atoms in molecules, natural bond orbital (NBO) and noncovalent interaction index analysis.