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Nuclear magnetic resonance VI. Some quantitative applications of carbon-13 NMR spectroscopy to phenylindoles

Kernresonanzspektroskopie, 6. Mitt. Einige quantitative Anwendungen der13C-NMR-Spektroskopie auf Phenylindole

  • Organische Chemie Und Biochemie
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Summary

The number of carbons represented by each signal of the phenylindoles1,4, and5 is measured quantitatively by integration of their13C NMR spectra, recorded after adding chromium(III) acetylacetonate to the sample solutions as a paramagnetic relaxation agent. Their carbon chemical shifts are assigned unambiguously; the literature assignments of4 are confirmed. By a comparative study of the carbon chemical shifts of1,4, and5, those of2 and3 are also assigned. Theortho carbons of the phenyl group of4 resonate upfield with respect to thepara carbon. Theortho carbons of the 2- and 3-phenyl moieties of1–3 and5, however, are found to absorb downfield from the correspondingpara carbons, probably because of steric and/or electronic effects exerted by their neighbouring phenyl group.

Zusammenfassung

Die Anzahl der durch jedes Signal der Phenylindole1,4 und5 repräsentierten Kohlenstoffatome wird durch Integration der nach Zusatz von Chrom(III)acetonylacetat als Relaxationsreagens aufgenommenen13C-NMR-Spektren bestimmt. Ihre chemischen Verschiebungen werden eindeutig zugeordnet; die Literaturwerte für4 werden bestätigt. Durch eine vergleichende Untersuchung der13C-chemischen Verschiebungen von1,4 und5 können jene von2 und3 ebenfalls zugeordnet werden. Dieortho-Kohlenstoffe der Phenylgruppe von4 sind gegenüber denpara-Kohlenstoffatomen zu höherem Feld verschoben. Für die 2- und 3-Phenyl-Substituenten von1–3 und5 kehren sich die Verhältnisse um, wahrscheinlich wegen sterischer und/oder elektronischer Effekte der benachbarten Phenylgruppe.

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Author notes

  1. D. Ganguly

    Present address: Department of Chemistry, Florida State University, 32306, Tallahassee, Fl, USA

Authors and Affiliations

  1. Department of Chemistry, University College of Science, University of Calcutta, 700009, Calcutta, India

    K. M. Biswas, R. N. Dhara, H. Mallik, S. Halder, A. Sinha-Chaudhuri, A. Saha, D. Ganguly, P. De & A. S. Brahmachari

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  1. K. M. Biswas
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  2. R. N. Dhara
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  4. S. Halder
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  5. A. Sinha-Chaudhuri
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  6. A. Saha
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  7. D. Ganguly
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  8. P. De
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  9. A. S. Brahmachari
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Biswas, K.M., Dhara, R.N., Mallik, H. et al. Nuclear magnetic resonance VI. Some quantitative applications of carbon-13 NMR spectroscopy to phenylindoles. Monatsh Chem 127, 111–116 (1996). https://doi.org/10.1007/BF00807416

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  • DOI: https://doi.org/10.1007/BF00807416

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