Open Access3(4)-Amino-4(3)-nitro-1,2,5-oxadiazole-2-oxides and their Ring-opened Isomers-A DFT Treatment
Author(s) -
Lemi Türker
Publication year - 2020
Publication title -
earthline journal of chemical sciences
Language(s) - English
Resource type - Journals
ISSN - 2581-9003
DOI - 10.34198/ejcs.4120.3551
Subject(s) - oxadiazole , nitroso , ring (chemistry) , chemistry , tautomer , nitro , imine , homo/lumo , nitroso compounds , oxime , computational chemistry , molecular orbital , density functional theory , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis , alkyl
Amino and nitro substituted 1,2,5-oxadiazole-2-oxide isomers and their ring-opened nitroso forms have been subjected to density functional treatment at the level of B3LYP/6-311++G(d,p). The transition states for the ring opening processes are obtained and the corresponding activation energies have been calculated. Also, 1,3- and 1,5-proton tautomerism yielding imine, oxime and aci forms are investigated. For all the structures, the stabilities, the HOMO, LUMO energies and the interfrontier molecular orbital energy gaps are obtained and the effects of substituents (NH2 and NO2) are discussed.