• Substituent effects on carbon-13 NMR chemical shifts of side chain carbonyl carbons of 4-substituted 1-naphthamides

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      https://www.ias.ac.in/article/fulltext/jcsc/098/03/0207-0212

    • Keywords

       

      Naphthamides; substituent chemical shifts; reverse substituent effect; π-polarisation

    • Abstract

       

      Substituent induced13C NMR chemical shifts of side chain carbonyl carbons of several 4-substituted 1-naphthamides have been measured in DMSO-d6 solvent. Analysis of the substituent induced chemical shifts by the DSP equation gave the regression equation. Both {ie207-1} and {ie207-2} values were negative. The negative sign on {ie207-3} term indicates the operation of a reverse substituent effect and that π-polarisation is the important mechanism for the transmission of substituent effects by inductive effect. Theperi-hydrogen interaction in naphthamides forces the amide group out of the plane of the naphthalene ring.

    • Author Affiliations

       

      K Rajasekaran1 C Gnanasekaran1 T C Wong2

      1. Department of Chemistry, VHNSN College, Virudhunagar - 626 001, India
      2. Department of Chemistry, University of Missouri, Columbia, USA
    • Dates

       
  • Journal of Chemical Sciences | News

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