engleski

Molecular and electronic structure of benzannulated isobenzofurans

Density functional theory (DFT) calculations at the B3LYP/6-31G* level of theory for isobenzofuran 1 and eleven benzannulated derivatives have been performed in order to compare their relative reactivities as dienes in Diels-Alder reactions. The transition state (TS) energies for their reactions with ethylene have been determined and shown to form a linear correlation between activation energies and structure count (SC) ratios. TS energies as method for comparison of diene reactivities can be applied to IBFs bearing substituents on the ring as well as those containing heteroatoms, for which SC ratio method fails. Different measures of aromaticity of benzannulated IBFs indicate the decrease in the aromaticity, what is reflected on their reactivity as a dienes in Diels-Alder reaction.

DFT; calculations; transition states; cycloadditions; isobenzofurans

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