Scholarlink

<p><i>N</i>- and <i>S</i>-alkyl derivatives were synthesized from 5-phenyl-1,3,4-oxadiazole-2-thione and alkyl halides. The structures were elucidated using <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, as well as X-ray diffraction (XRD) analysis. Based on XRD and DFT data, the aromaticity of the 1,3,4-oxadiazole ring was evaluated. Redistribution of the <i>π</i>-electron system in the pseudoaromatic 1,3,4-oxadiazole-2-thione fragment of the <i>N</i>- and <i>S</i>-alkyl derivatives, relative to the parent 5-(phenyl-1,3,4-oxadiazole-2(3<i>H</i>)-thione, was observed. The aromaticity of the 1,3,4-oxadiazole ring in the <i>N</i>- and <i>S</i>-alkyl derivatives of 5-phenyl-1,3,4-oxadiazole-2-thione decreases, with the <i>S</i>-derivatives exhibiting lower aromaticity than the <i>N</i>3-derivatives according to the calculations. The theoretically calculated aromaticity values for all known 1,3,4-oxadiazole derivatives, using a specific publicly available Bird method by Multiwfn package, allow chemists to identify patterns and draw conclusions.</p> Graphical abstract <p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Synthesis, structure, and assessment of aromaticity of the 1,3,4-oxadiazole ring in N- and S-alkyl derivatives of 5-phenyl-1,3,4-oxadiazol-2-thione using the Bird index

  • 期刊论文

  • 发表日期：

    2025年5月7日

查看全文
  • Abdukhakim A. Ziyaev,
  • Rasul Ya. Okmanov,
  • Utkir S. Makhmudov,
  • Alisher G. Eshimbetov,
  • Turdibek T. Toshmurodov,
  • Bakhodir Tashkhodzhaev,
  • Khamid U. Khodjaniyazov

摘要

N- and S-alkyl derivatives were synthesized from 5-phenyl-1,3,4-oxadiazole-2-thione and alkyl halides. The structures were elucidated using 1H and 13C NMR spectroscopy, as well as X-ray diffraction (XRD) analysis. Based on XRD and DFT data, the aromaticity of the 1,3,4-oxadiazole ring was evaluated. Redistribution of the π-electron system in the pseudoaromatic 1,3,4-oxadiazole-2-thione fragment of the N- and S-alkyl derivatives, relative to the parent 5-(phenyl-1,3,4-oxadiazole-2(3H)-thione, was observed. The aromaticity of the 1,3,4-oxadiazole ring in the N- and S-alkyl derivatives of 5-phenyl-1,3,4-oxadiazole-2-thione decreases, with the S-derivatives exhibiting lower aromaticity than the N3-derivatives according to the calculations. The theoretically calculated aromaticity values for all known 1,3,4-oxadiazole derivatives, using a specific publicly available Bird method by Multiwfn package, allow chemists to identify patterns and draw conclusions.

Graphical abstract