Bulletin of the Korean Chemical Society

  • 제23권9호
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  • Pages.1241-1255
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  • 2002
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Correlation of Chemical Shifts with Substituent Parameters in N-Benzyl Derivatives of Pyrrole,3a,7a-Dihydroindole,and Indole Esters

  • 발행 : 2002.09.20
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초록

Series of m- and p-substituted benzyl derivatives of pyrrole, tetramethyl 1-benzyl-3a,7a-dihydroindole-2,3,3a,4-tetracarboxylate, and trimethyl 1-benzylindole-2,3,4-tricarboxylate were prepared and their 13C NMR spectra were obtained in 0.1 M solutions of chloroform-d. Both single substituent parameter and dual substituent parameter analyses were carried out to correlate the substituent chemical shifts. The ${\beta}$ carbon of the indole series showed the most profound substituent effect dependence as well as the best correlation. The results are explained by the hyperconjugation of the benzyl methylene group.

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참고문헌

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피인용 문헌

  1. Infrared and nuclear magnetic resonance properties of benzoyl derivatives of five-membered monoheterocycles and determination of aromaticity indices vol.40, pp.5, 2002, https://doi.org/10.1002/jhet.5570400504
  2. Use of Correlation of 1H and 13C Chemical Shifts of N-Arylsuccinanilic Acids,N-Arylsuccinimides, N-Arylmaleanilic Acids, and N-Arylmaleimides with the Hammett Substituent Constan vol.30, pp.10, 2009, https://doi.org/10.5012/bkcs.2009.30.10.2351
  3. Substituent effect study on the experimental 13C NMR chemical shifts of 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazoles vol.1193, pp.None, 2002, https://doi.org/10.1016/j.molstruc.2019.04.121
  4. Synthesis and substituent effect study on 13C NMR chemical shifts of 4-(substitue-phenyl)-6-methyl-3-phenyl-4H-1,2,4-oxadiazin-5(6H)-one vol.1250, pp.p2, 2002, https://doi.org/10.1016/j.molstruc.2021.131787