The Stone-Wales rearrangement is analyzed using a newly developed continuous chirality measure. In enantiomerization reactions of chiral fullerenes we find an approximately linear correlation between π-energy and the chirality content of the molecule. These correlations show that the sensitivity to chirality change increases for larger fullerenes. We show its predictive properties and provide an explanation for it on the basis of another observation; namely, that the chirality value decreases monotonically with fullerene size. Comparison of the enantiomerization to other isomerizations of fullerenes is made.