Synthesis and Structures of 5-(2,4-Dichlorophenyl)-1,3,4-Oxadiazole-2-Thione Alkyl Derivatives and Estimation of the Aromaticity of the Oxadiazole Ring
R. Ya. OkmanovYunusov Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, UzbekistanU.S. MakhmudovAcademy of Sciences of Uzbekistan, Tashkent, UzbekistanA. A. ZiyaevYunusov Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, UzbekistanT. T. ToshmurodovYunusov Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, UzbekistanB. TashkhodzhaevYunusov Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Tashkent, UzbekistanA. G. EshimbetovSadykov Institute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Tashkent, UzbekistanKhamid U. KhodjaniyazovFaculty of Chemistry, Mirzo Ulugbek National University of Uzbekistan, Tashkent, Uzbekistan
ABI
Abstract
A series of 5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thione alkyl derivatives are obtained. Structures of the products are determined from the IR, UV, 1H and 13C NMR spectroscopic results together with single crystal X-ray diffraction (XRD). The aromaticity of the 1,3,4-oxadiazole ring is estimated by single crystal XRD and DFT calculations using the Multiwfn program package. It is found that in S-derivatives, the π electron system is redistributed in the pseudo-aromatic 1,3,4-oxadiazole-2-thione moiety relative to initial 5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2(3H)-thione. In the S-derivatives of 5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thione the aromaticity of the 1,3,4-oxadiazole heterocycle is lower than that in N3-derivatives.
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