Web Release Date: April 3,
Density Functional Study of
2-[(R-Phenyl)amine]-1,4-naphthalenediones
and
Departamento de Química, CINVESTAV, Avenida Instituto Politécnico Nacional 2508, A.P. 14-740 México D.F. 07000, México, Facultad de Química, Departamentos de Bioquímica y Fisicoquímica, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, México, and Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, México.
Received November 12, 2006
Abstract:
The molecular and electronic structures of a series of 2-[(R-phenyl)amine]-1,4-naphthalenediones (R = m-Me, p-Me, m-Et, p-CF3, p-Hex, p-Et, m-F, m-Cl, p-OMe, p-COMe,
p-Bu, m-COOH, p-Cl, p-COOH, p-Br, m-NO2, m-CN, and p-NO2) and their anions are investigated
in the framework of density functional theory. The calculations are of all-electron type using a
double zeta valence polarization basis set optimized for density functional theory methods. The
theoretical study shows that all compounds are nonplanar. The nonplanarity can be rationalized
in terms of occupied 
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 generalized
gradient corrected functionals. Structural parameters, harmonic vibrational frequencies, and
adiabatic and vertical electron affinities as well as orbital and spin density plots of the studied
compounds are presented.
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