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Report | Regular issue | Vol 19, No. 12, 1982, pp.2331-2338
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2331
A Study of the Structure of 4-Arylazo Derivatives of 2-Phenyl-5-oxazolone

Ahmad S. Shawali, Abdou O. Abdelhamid, Nada F. Ahmad, and Cyril Párkányi

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt

Abstract

Spectroscopic methods (1H NMR and IR) were used to determine the structure of the 4-arylazo derivatives of 2-phenyl-5-oxazolone. The data indicate that such compounds exist in the chelated hydrazone form 1A(z). The 15N isotopomer of compound 1a confirms the hydrazone structure. Also, the HMO method has been used to study tautomerism in such compounds. The results are in full agreement with the spectral data, the hydrazone form 1A(z) being most stable. It is further shown that both the intermolecular and intramolecular hydrogen bonding and electron-withdrawing substituents favor the hydrazone tautomer.