Excellent correlations of Hammett substituent constants (sigmaR) of a series of N-(R-substituted aryl) -2,6-, 2,5-, and 5,6- dichloronicotinamides with polarographic half-wave potentials were observed. Although the correlations demonstrate that all three series of amides experience comparable sensitivity to the R groups at the carbonyl reduction site, the relative ease of reduction varies according to the chlorine substitution pattern on the pyridine ring. These differences are suggested to be due to combinations of mesomeric, inductive, and field effects which operate differently in the three systems. Correlation analysis also revealed that Hammett heteroatomic replacement constants previously determined by NMR studies are valid in the present polarographic studies.
Persons, Cecil C.; Shaikh, Ali U.; Shiflett, Julie; and Setliff, Frank L.
"Hammett Correlations of Half-Wave Reduction Potentials in a Series of N-(Aryl substituted)-Dichloronicotinamides,"
Journal of the Arkansas Academy of Science: Vol. 48
, Article 27.
Available at: http://scholarworks.uark.edu/jaas/vol48/iss1/27