Synthesis, structural determination, Hirshfeld surface analysis, 3D energy frameworks, electronic and (static, dynamic) NLO properties of o-Nitroacetanilide (o-NAA): A combined experimental and quantum chemical study
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Date
2021
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Abstract
o-Nitroacetanilide (o-NAA), an organic crystal, was synthesized and fully characterized by means of single-
crystal XRD, FTIR, UV–visible,
1
H and
13
C NMR spectroscopic techniques. Its molecular structure was optimized,
the
subsequent
electronic
properties,
the
spectroscopic
spectra
were
quantified
using
quantum
chemical
computations
by density functional theory calculations and compared with the experimental results. Furthermore,
the
Mulliken
atomic
charges
were
estimated
andthe
molecular
electrostatic
potential
map
was
plotted
in
order
to
identify
the
chemical
reactive
sites.
To
study
the
nonlinear
optical
(NLO)
activity
of
o-NAA,
the
electric
dipole
moment,
the
static
and
dynamic
polarizability
and
hyperpolarizabilities
were
computed
indicating
that
it
could
be considered as a good candidate for NLO applications. The hydrogen bonding and the non-classical
intermolecular interactions were investigated by performing a Hirshfeld surface analysis and their contributions
were
analyzed
via
the
2D-Fingerprint
plots,
thus
revealing
that
the
crystal
structure
of
the
studied
molecule
is
mainly built up of H…H, H…O/O…H, H…C/C…H and C…O/O…C close contacts. From the 3D-molecular
energy frameworks analysis, the lattice energy of the compound was found to be 95.15 kJ.mol
, and has
exhibited stabilizing strong C
–
H…O, N
–
H…C, lp…lp, lp…π and π…π interactions.
1