PABA is para-aminobenzoic acid. This is a "classical" push-pull
substituted molecule. The amino group donates (pushes) and carboxyl group
accepts (pulls). Compounds with push-pull substitution have low
HOMO-LUMO gaps. PAPA was used as a UV-B absorbing sunscreen. Notice that
the amino group is NOT sp2-hybridized but the N-atom is clearly
pyramidal!
The MO eigenvalues of PABA are provided in the file behind the
link eigenvalues. Find the eigenvalues of the HOMO
and the LUMO and compare the HOMO-LUMO gap to the respective gaps in
aniline and benzoic acid.