Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Structural Studies by NMR (Ⅰ). Conformations and Configurations of ${\alpha},{\beta}$-Unsaturated Phenylhydrazones

NMR에 의한 입체구조에 관한 연구 (제1보). ${\alpha},{\beta}$-Unsaturated Phenylhydrazones의 Conformation과 Configuration에 대하여

  • Lee Hak-ki (College of Engineering, Kyungpook National University) ;
  • Lim Yong Jin (College of Engineering, Kyungpook National University) ;
  • Choi Jung Do (College of Engineering, Kyungpook National University)
  • Published : 1974.06.30
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Abstract

Conformations and cofigurations were studied for some ${\alpha},{\beta}$-unsaturated phenylhydrazones which have similar structures to the stucture of butenedial bistosylhydrazone, a precursor of tetrahedrane, by the analysis of their nmr spectra. The chemical shift difference between two solvents, benzene and aliphatic solvents, was applied for the assigning syn and anti structures of phenylhydrazone isomers as a convenient method. In this work, it was found that the phenylhydrazones have syn configurations and also found that the dihedral angles of $CH_a-CH_b$ are around $150^{\circ}$ at room temperature from the the interpretation of the vicinal spin-spin coupling constants. These results were discussed in concerning with their conformations.

저자들은 tetrahedrane생성의 전구체인 t-butenedial bistosylhydrazone의 입체적인 구조를 연구할 목적으로 이의 유사한 구조인 ${\alpha},{\beta}$위치에 이중결합을 가지고 있는 몇 가지 phenylhydrazone을 합성하고 이들의 형태 및 배위를 nmr spectra의 해석으로부터 구명했다. 벤젠용매와 aliphatic solvent(CC14, DMSO)에서의 chemical shift의 차이로 부터 이들 물질이 syn-configuration을 가지고 있음을 알았으며 spin-spin coupling constant 로부터 이들 물질의 형태를 고찰하였다.

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References

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