The
molecular
and electronic structures of a series of 2-[(R-phenyl)a
mine]-1,4-naphthalenediones (R =
m-Me, p-Me,
m-Et, p-CF
3, p-Hex, p-Et,
m-F,
m-Cl, p-OMe, p-COMe,p-Bu,
m-COOH, p-Cl, p-COOH, p-Br,
m-NO
2,
m-CN,
and p-NO
2)
and their anions are investigatedin the fra
mework of density functional theory. The calculations are of all-electron type using adouble zeta valence polarization basis set opti
mized for density functional theory
methods. Thetheoretical study shows that all co
mpounds are nonplanar. The nonplanarity can be rationalizedin ter
ms of occupied
![](/i<font color=)
mages/gifchars/pi.gif" BORDER=0 > orbitals. A linear correlation between the
measured half-wave potentials
and the calculated gas-phase electron affinities is found. It holds for local as well as generalizedgradient corrected functionals. Structural para
meters, har
monic vibrational frequencies,
andadiabatic
and vertical electron affinities as well as orbital
and spin density plots of the studiedco
mpounds are presented.