Semi-empirical (PM3 and AM1) and ab initio molecular orbital calculations of 1,2,4-oxadiazoles, 4,5-dihydro-1,2,4-oxadiazoles and 4,4-di- n-butyl-2-phenylbenzo-1,3-oxazine

Abstract

Molecular orbital calculations using semi-empirical (PM3 and AM1) and ab initio (HF/6-31G) types have been carried out on several 3,5-disubstituted 1,2,4-oxadiazoles 1a– d, 5- n-butyl-3,5-diaryl-4,5-dihydro-1,2,4-oxadiazoles 2a– d, and 4,4-di- n-butyl-2-phenylbenzo-1,3-oxazine 3. A comparison of the results by the two computational procedures has been made. Transformation of the oxadiazole ring to 4,5-dihydro-1,2,4-oxadiazole having both aryl and n-butyl groups at C-5 exhibited interesting conformational features. Also, examination of 1,3-oxazine 3 gave an idea about the structure of this compound. The rotational barrier of each phenyl group in 1a and 1d has been calculated using the ab initio method HF/6-31G(d).