Substituent Effects on 15N and 17O NMR Chemical Shifts in 4′-Substituted <i>trans</i>-<i>NNO</i>-Azoxybenzenes

DOI DOI PDF 被引用文献3件 参考文献44件 オープンアクセス
  • Sawada Masami
    Material Analysis Center, the Institute of Scientific and Industrial Research, Osaka University
  • Takai Yoshio
    Material Analysis Center, the Institute of Scientific and Industrial Research, Osaka University
  • Tanaka Takanori
    Material Analysis Center, the Institute of Scientific and Industrial Research, Osaka University
  • Hanafusa Terukiyo
    Material Analysis Center, the Institute of Scientific and Industrial Research, Osaka University
  • Okubo Masao
    Department of Chemistry, Faculty of Science and Engineering, Saga University
  • Tsuno Yuho
    Department of Chemistry, Faculty of Science, Kyushu University

書誌事項

タイトル別名
  • Substituent effects on 15N and 17O NMR chemical shifts in 4'-substituted trans-NNO-azoxybenzenes.
  • ChemInform Abstract: Substituent Effects on 15N and 17O NMR Chemical Shifts in 4′‐Substituted trans‐NNO‐Azoxybenzenes

説明

15N and 17O NMR spectra have been measured for a series of 4′-substituted trans-NNO-azoxybenzenes (AZOXY) and the obtained substituent chemical shift (SCS) values have been analyzed by means of the LSFE equation. Both the resonance and the polar contribution of substituents are important in determining the 15N(β) SCS and the adjacent terminal 17O SCS in the –Nα=Nβ(O)– function of the AZOXY set. The resonance contributions of the AZOXY sets differ from those of the corresponding PYNO sets in view of a depressed pi-acceptor resonance contribution. That is, the resonance susceptibility ratio in the LSFE equation, ρπ+⁄ρπ−, varies from 1.4 (PYNO) to 2–4 (AZOXY) for both 15N and 17O SCS. The results are compared with the 13C SCS of the corresponding positions in the relevant aromatic side-chain systems, and characterized in terms of repulsive pi-acceptor interaction between the substituents and the side-chain pi-electron systems. The importance of such dual resonance susceptibility has been shown for understanding characteristic features of the 15N and the adjacent 17O SCS.

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