Synthesis and Electronic Structure of New Aryl- and Alkyl-Substituted 1,3,4-Oxadiazole-2-thione Derivatives

Authors

FERAY AYDOĞAN
ZUHAL TURGUT
NÜKET ÖCAL
SAFİYE SAĞ ERDEM

DOI

-

Abstract

New 5-alkyl and 3-(2,4-dimethylphenyl) substituted 1,3,4-oxadiazole-2-thione derivatives were synthesized by the ring closure reactions of various acylhydrazides with carbon disulphide. Mannich bases for some of these compounds were also synthesized by condensation with benzaldehyde and primary amines. All new compounds were characterized by spectral data. Most of them were tested for their antibacterial and antituberculostatic activity. Molecular orbital calculations at the HF/6-31G** level were also performed to determine the optimized geometrical structures. Results indicated electron delocalization over several atoms of the ring. An additional study on the tautomeric equilibrium between 1,3,4-oxadiazole-2-thione and its thiol form showed that the thione tautomer is favoured by 9.616 kcal/mole in the gas phase and by 12.123 kcal/mole in aqueous medium.

First Page

159

Last Page

170

Recommended Citation

AYDOĞAN, FERAY; TURGUT, ZUHAL; ÖCAL, NÜKET; and ERDEM, SAFİYE SAĞ (2002) "Synthesis and Electronic Structure of New Aryl- and Alkyl-Substituted 1,3,4-Oxadiazole-2-thione Derivatives," Turkish Journal of Chemistry: Vol. 26: No. 2, Article 3. Available at: https://journals.tubitak.gov.tr/chem/vol26/iss2/3