Theoretical Study on the Diels–Alder Reaction of Fullerenes: Analysis of Isomerism, Aromaticity, and Solvation

Fullerenes are reactive as dienophiles in Diels–Alder reactions. Their distinctive molecular shape and properties result interesting sometimes elusive reaction patterns. Herein, to contribute the understanding of fullerene reactivity, we evaluate energies reactions for cycloadditions C60, C70, IC60MA with anthracene (Ant), by means DFT computational analysis vacuum solution. The methods used showed little differentiation between reactivity different fullerenes. C70-Ant adducts where addition takes place near edge were found be most stable regioisomers. For IC60MA-Ant adducts, calculated increase order: equatorial > trans-3 trans-2 ? trans-4 trans-1 cis-3 cis-2. change functional suggests existence stabilizing dispersive interactions surface addends. HOMA (harmonic oscillator model aromaticity) indicated an aromaticity hexagons adjacent bonded addend. This is bigger rings bisadduct isomers that simultaneously both addends, which helps explain extra stability isomers. Solvation m-xylene decreases exothermicity studied but has distinguishing effect on possible Thermal corrections reduce ~10 kJ?mol?1.