Crystal Structure Analysis and Computational Study of 4,5-Dihydro-1,2,4-Oxadiazoles

Author:

Asgari Mehrnoosh,memarian Hamid Reza,Sabzyan Hassan,Rudbari Hadi Amiri,Blacque Olivier

Publisher

Elsevier BV

Reference54 articles.

1. The crystal packing analysis revealed the presence of a pure R-enantiomer, a pure S-enantiomer, and a racemic mixture, for DHOZs 1, 2 and 3, respectively. For justification of these experimental observations, imino-oxime intermediates are proposed to be involved in their synthesis reactions. Structures of these intermediates are optimized at the B3LYP/6-311++G(d,p) level of theory and studied. Based on these studies, the steric effect of the C 5 -aryl ring contributes to the observed stereoselectivity of the intramolecular nucleophilic attack (S N i) of the O-atom of the hydroxy group in the amidoxime moiety on the re-and si-faces of the imine N 4 =C 5 double bond, resulting in the formation of the specific enantiomer of these DHOZs. The QTAIM and NCI plot analyses of the dimeric forms of the crystal structures illustrated that these interactions consist of weakmedium strength Van der Waals (VdW) and hydrogen bond (HB) interactions;� H/H���o;Conclusion Different intra-and intermolecular H-bond interactions,2004

2. Room temperature synthesis of bioactive 1,2,4-oxadiazole;S V Baykov;Int. J. Mol. Sci,2023

3. Inhibition of 3-hydroxykynurenine transaminase from aedes aegypti and anopheles gambiae: A mosquito-specific target to combat the transmission of arboviruses;L G Maciel;ACS Bio. Med. Chem. Au,2023

4. Discovery of novel n-hydroxy-1,2,4-oxadiazole-5-formamides as ASM direct inhibitors for the treatment of atherosclerosis;K Yang;J. Med. Chem,2023

5. oxadiazole ring system-a novel building block for creating energetic compounds;H Dou;J. Chem. Eng,2022

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