Experimental and computational spectroscopic studies of 3,5-disubstituted 4,5-dihydro-1,2,4-oxadiazoles

被引：12
作者：
Asgari, Mehrnoosh [1 ]
Memarian, Hamid R. [1 ]
Sabzyan, Hassan [1 ]
机构：
[1] Univ Isfahan, Dept Chem, Esfahan 8174673441, Iran
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2020年 / 1207卷
关键词：
Dihydrooxadiazoles; Substituent effects; Spectroscopic studies; (TD)DFT/6-311++G(d; p); Conformational analysis; MOLECULAR-ORBITAL CALCULATIONS; INDUCED OXIDATION; NMR; 1,2,4-OXADIAZOLES; DFT;
D O I：
10.1016/j.molstruc.2020.127820
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Some 3,5-disubstituted 4,5-dihydro-1,2,4-oxadiazoles (DHOZs) were synthesized, and steric and electronic effects of the substituents on the heterocyclic ring C3- and C5-positions were investigated using the NMR and UV-Vis spectroscopies, and (TD)DFT/6-311++G(d,p) computations. The NMR and UV-Vis spectroscopic characteristics of the synthesized compounds could be explained in terms of the pi- and sigma- electronic effects of the C3- and C5-aryl substitutions on the heterocyclic ring, respectively. Computational NMR chemical shifts and spin-spin coupling constants of the C5-H and N4-H protons display a Karplus correlation with corresponding H-C5-N4-H dihedral angle. The experimental and computational H-1 NMR chemical shifts of the C5-H proton show very good compatibility. Conformational analysis on the o-nitro and o-methoxyphenyl C5-substituted DHOZs showed intramolecular interactions affecting their structural and spectroscopic features. (C) 2020 Elsevier B.V. All rights reserved.
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页数：18
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