Theoretical investigation of the effect of substituent on the cyclicopen tautomerism in 5-phenyl-1,2,3,4-oxatriazole: Molecular orbital treatment, DFT calculationAuthor(s): Wael A.Zordok
The effect of substituents R= H, Cl, OH, CH3, NO2 and CN in 5-phenyl-1,2,3,4-oxatriazole, on the oxatriazoleï« azide tautomerism, was investigated at B3LYP/6-311G** level of (DFT) method. The structural and energetic parameters were calculated at optimized geometry. For all substituents the p-substituent of benzoyl azide forms are largely favored. There is no large difference in dipole moment between two conformers c oxatriazole and aroyl azide. The reaction is spontaneous and the rate of reaction in case of CH3 group is lower than others, with higher energy barrier ÄE= 2.71Kcal/mol, while the rate of reaction is faster than others in case of CN group, with lower energy barrier 2.4Kcal/mol. The reaction of cyclic-open conversion of 5-phenyl-1,2,3,4-oxatriazole to corresponding aroyl azide is exothermic reaction.