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Studies on Dithiocarbamates : Part X. Synthesis and Spectral Characteristics of Mesoionic 4-phenyl-5-aryl-1,3,4,-thiadiazoles

Authors: P. B. Talukdar; S. K. Sengupta;

Studies on Dithiocarbamates : Part X. Synthesis and Spectral Characteristics of Mesoionic 4-phenyl-5-aryl-1,3,4,-thiadiazoles

Abstract

A series of the titled compounds have been synthesized with well-behaved meta and para-substituents on the phenyl ring at C5 and their spectral data on long wavelength π→π* transition as well as the stretching frequency of C-S band have been examined in the light of linear free energy relationship. Thus, Hammett \(\sigma\rho\) relation was valid only with exalted values for NO2 and CN groups indicating appreciable internuclear conjugation, comparable to biphenyl system, between the planar mesoionic ring and the phenyl ring at C5. Strong dipolar interactions in solution have been demonstrated by the use of solvents of graded polarity. In the UV region λmax around 275 and 250 m\(\mu\) have been assigned to phenyl groups at N4 and C5 respectively.

Keywords

Mesoionic compounds, Spectral measurements, Dithiocarbamates, Solvent Effect

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