Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Substituent Chemical Shifts of (E)-1-Aryl-3-thienylpropen-1-ones

  • HanLee, In-Sook (Department of Science Education, Kangwon National University) ;
  • Jeon, Hyun-Ju (Department of Chemistry, Kangwon National University) ;
  • Yu, Ji-Sook (Department of Chemistry, Kangwon National University) ;
  • Lee, Chang-Kiu (Department of Chemistry, Kangwon National University)
  • Received : 2010.02.22
  • Accepted : 2010.03.25
  • Published : 2010.06.20
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Abstract

Substituent chemical shifts were examined for the 2- and 3-thiophene derivatives of chalcone and compared to the thiophene series of derivatives with the phenyl series. The chemical shift values for the ${\alpha}$-carbons of the enones showed and inverse correlation with the Hammett $\sigma$ values, but the correlation coefficients were moderate (r = 0.836 - 0.878). On the other hand, the $\beta$-carbons showed a normal correlation with excellent correlation coefficients (r = 0.994). The absolute magnitude of the $\rho$ values for the $\alpha$-carbon are about half of those of the $\beta$-carbon. The observation may be the result of a through-space transition of the electronic effect of the substituents in addition to the through bond transition.

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References

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