Spectral and Quantum-Chemical Study of the 1,3-Dipolar Cycloaddition Reaction of Phenyl Azide and Chalcone
Keywords:
Dipolar Cycloaddition, Phenyl Azide, Chalcone, activation energy, DFTAbstract
A study of 1,3-dipolar cycloaddition reaction of phenyl azide and chalcone was
carried out theoretical and experimental in ethanol by DFT/B3LYP (3-21G) method,
without and with CuCl as catalyst. The isolated and purified products were
characterized by spectral methods, by IR, 1H-NMR, 13C-NMR, Cosy and Dept-135.
Theoretical study of the reaction was achieved using Gaussian03 program based on a
density function method, DFT/B3LYP (3-21G) . The structural, electronic and
spectral properties were calculated for the more probable product.
The experimental and theoretical results were consistent, the title was found to be
nonspontaneons under standard conditions (T=298,15 K , P= 1 atm), but it toke place
in ethanol under reflux in the presence of CuCl, the reaction was completely
regioselective and the expected product was formed in high yield 75%, formula
C21H17N3O and m.p 164-165C0.
