Structural Characterization of 6-Bromo-5-nitroquinoline-1-oxide: A Quantum Chemical Study and XRD Investigations
Abstract
The chemical properties of recently synthesized
6-bromo-5-nitroquinoline-1-oxide under a mild reaction condition by regioselective
nitration of 6-bromoquinoline-1-oxide
at C5 on going our research were investigated as theoretical. The crystal
structure of 6-bromo-5-nitroquinoline-1-oxide, C9H5BrN2O3, was determined
by X-ray analysis. Crystallized in Pmc21
in the orthorhombic space group with a
= 13.6694 (13) Å, b = 9.6036 (10)
Å, c = 14.1177 (16) Å, Z = 8, Dx = 1.929 mg/m3. In this study, theoretical calculations were performed using the
GaussView 4.1 molecular imaging program and the Gaussian03W packet program. In
the ground state, stable structures of the wholes molecule in the gaseous phase
are investigated based on Density Functional Theory (DFT). Molecularly
optimized geometries, dipole moments, charge density, thermodynamic properties
(heat capacity, enthalpy, entropy), chemical shift values (1H
NMR and 13C NMR), energies, molecular
electrostatic potentials and frontier orbitals (HOMO and LUMO)
B3LYP/6-311G(d,p) base set. Thus, the results obtained by the X-ray diffraction
method are supported by theoretical foundations. Finally, the distribution of
interactions between molecules in the crystal structure of
6-bromo-5-nitroquinoline-1-oxide (3) was
investigated by analysis using Hirshfeld surface production and two-dimensional
fingerprinting.
Keywords
Nitration,N-oxidation,Functionalization,XRD,DFT,6-Bromoquinoline-1-oxide
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