An Anomalous Hammett Correlation for a Series of Substituted 3-Benzyl-2-phenyl-1,3-thiazolidin-4-ones

  •  Daniel McGarity    
  •  John Tierney    
  •  Anthony Lagalante    


A series of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one derivatives, with substituents at the N-benzyl site, was synthesized and characterized. Excluding the p-MeO and m-Br derivatives, distinct correlations between Hammett constant ? and 13C substituent chemical shifts were observed in the C2, C4, and C5 carbons in the thiazolidin-4-one ring. This was unexpected because the transmission of substituent effects appears to be occurring via the sp3 hybridized N-benzyl carbon. No discernible correlation was seen for the N-benzyl carbon; the carbon through which the effects were occurring. Correlations for substituent chemical shifts to Swain Lupton substituent parameters r and f constants were also attempted. Similar to the Hammett correlations, C2, C4, and C5 showed a reasonable degree of correlation with minimal to no improvement over Hammett constants; similarly, as with the Hammett correlations, the benzyl carbon exhibited no correlation with Swain Lupton parameters.


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  • ISSN(Print): 1916-9698
  • ISSN(Online): 1916-9701
  • Started: 2009
  • Frequency: semiannual

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