Theoretical study of the corannulene ozonolysis and evaluation of the various reaction paths

چکیده مقاله

The 1,3-dipolar cycloaddition of ozone to corannulene was investigated by quantum calculations at B3LYP/6-311(d,p) level of theory. The reaction of ozone with various kinds of CAC bond of corannulene in twelve pathways was investigated. The rate constants for all paths were calculated by using energy barriers and partition functions. Energy barrier of the addition of ozone to rim, flank, spoke and hub positions were obtained equal to 50.74, 55.27, 105.34 and 83.95 kJ mol 1 , respectively. Our theoretical investigation shows that rim position is the best for functionalization with ozone molecules. Corannulene epoxide with a triangle cycle in the rim, spoke and hub positions but not in flank position that formed through a Criegee intermediate is major product.