Author/Authors :
Khojastehnezhad, Amir Islamic Azad University Mashhad, Iran , Eshghi, Hossein Department of Chemistry - Faculty of Sciences - Ferdowsi University of Mashhad, Mashhad, Iran , Moeinpour, Farid Department of Chemistry - Bandar Abbas Branch, Islamic Azad University, Bandar Abbas, Iran , Raoufi, Arastou Department of Chemistry - Mashhad Branch, Islamic Azad University, Mashhad, Iran
Abstract :
The mechanism (regioselectivity) of [3+2] cycloaddition reaction of indan-1-one enamines (1ad–1ce) with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous one-step mechanism with a nonpolar character. Theoretical data are in good agreement with the experimental results.
Keywords :
Regioselectivity , [3+2] Cycloaddition , Aryl nitrile oxide , DFT reactivity indices
