Journal
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
Volume 48, Issue 1, Pages 65-72Publisher
CHINESE CHEM SOC
DOI: 10.1002/jccs.200100012
Keywords
hydrazonoyl halides; 1,2,4-triazole-3-thione; thiohydrazonate esters; Forster cycle; Hammett equation; tautomerism
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7-Arylhydrazono[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazines 4 were synthesized from the reactions of 4-amino-5-phenyl-4H-[1,2,4]triazole-3-thiol 2 and 2-(2-naphthyl)-2-oxoethanehydrazonoyl bromides 1 and their acid dissociation constants pK and pK*, in the ground and excited states, respectively, were determined. Both pK and pK* constants were correlated by Hammett equation. The pK and the spectral data presented indicate that the title compounds exist predominantly in the hydrazone tautomeric form.
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