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and polarizability are greater than that of 4-(2,3,4-
trihydroxybenzylideneamino)antipyrine [66] and 2-methyl-
6-[2-(trifluorormethyl)phenyl-iminomethyl]phenol [73]. These
results indicate that title compound is a good candidate of
nonlinear optical material.
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(Z)-1-((4-Phenylamino)phenylamino)methylene)naphtha-
len-2(1H)-one has been synthesized and characterized by
IR, UV–Vis, and X-ray single-crystal diffraction. The
X-ray, IR, and UV–Vis spectral data for the title compound
show that the compound exists in the keto-amine tauto-
meric form, which is stabilized by the intramolecular
N–HꢀꢀꢀO hydrogen bond. The comparisons between the
calculated results and the X-ray experimental data indicate
that B3LYP method is better than HF method in evaluating
geometric parameters. The TD-DFT calculations lead to a
very closer agreement with the experimental absorption
spectra both gas phase and solvent media. Molecular
orbital coefficient analyses suggest that the electronic
spectrum corresponds to the p ? p* electronic transition.
The total energy of the title compound decreases with
increasing polarity of the solvent. The MEP map shows
that the negative potential site is on oxygen atom while the
positive potential sites are around the hydrogen atoms.
These sites give information about the region from where
the compound can have intermolecular interactions and
metallic bonding. The NBO analysis revealed that the
n(O1) ? r (N1–H1) interaction gives the strongest sta-
bilization to the system, and the major interaction for the
intermolecular O1ꢀꢀꢀN2 contact is n(O1) ? r (N2–H2).
This study also demonstrates that the title compound can be
used as a good nonlinear optical material.
˙
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Supplementary data
CCDC-795577 contains the supplementary crystallographic
data for the compound reported in this paper. These data
graphic Data Centre (CCDC), 12 Union Road, Cambridge
CB2 1EZ,UK; fax: ?44 1223 336033; e-mail: deposit@
ccdc.cam.ac.uk].
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