In this paper we report the application of quantum similarity measures as a
new means of quantitative characterization of molecular chirality. These m
easures, which are based on the quantitative comparison of electron density
functions of R and S enantiomeric structures, clearly demonstrate that the
presence, as well as the extent of chirality of these molecules, are refle
cted not only in the total electron densities, but also in the local shape
of small electron density fragments. The results may be regarded as a speci
al manifestation of the recently proven "holographic electron density theor
em", asserting that the complete information on the degree of molecular chi
rality is also contained in any fragment of the fuzzy, boundaryless electro
n density of molecules. The actual computational scheme provides a simple m
eans for potential applications in molecular similarity studies, where in a
ddition to the qualitative detection of the presence of chirality of enanti
omeric molecules and their fragments, the quantum similarity measures and t
he holographic approach are able to characterize the "extent" of chirality
quantitatively based on the actual electron densities. The proposed electro
n density approach for the quantification of chirality is more sensitive an
d provides more detail than the conventional nuclear framework approach.