TITLE:
Synthesis, Structural Study and Spectroscopic Characterization of a Quinolin-8-Yloxy Derivative with Potential Biological Properties
AUTHORS:
Elida Romano, María V. Castillo, Jorgelina L. Pergomet, Juan Zinczuk, Silvia A. Brandán
KEYWORDS:
(5-Chloro-Quinolin-8-Yloxy) Acetic Acid; Vibrational Spectra; Molecular Structure; Force Field; DFT Calculations
JOURNAL NAME:
Open Journal of Synthesis Theory and Applications,
Vol.2 No.1,
January
28,
2013
ABSTRACT:
We have prepared the (5-chloro-quinolin-8-yloxy) acetic acid and characterized it by using infrared, Raman and multi-dimensional nuclear magnetic resonance spectroscopies. The density functional theory (DFT) together with the 6-31G* and 6-311++G** basis sets were used to study its structure and vibrational properties. Three stable conformations of the compound were theoretically determined in gas phase and probably these conformations are present in the solid phase. The harmonic vibrational wavenumbers for the optimized geometries were calculated at the same theory levels. For a complete assignment of the observed bands in the vibrational spectra, the DFT calculations were combined with Pulay’s scaled quantum mechanical force field (SQMFF) methodology in order to fit the theoretical wavenumber values to the experimental ones. Besides, the force constants of the three conformers of (5-chloro-quinolin-8-yloxy) acetic acid were calculated and compared with those obtained by us for the 2-(quinolin-8-yloxy) acetic acid. In addition, the characteristics of the electronic delocalization of those structures were performed by using natural bond orbital (NBO), while the corresponding topological properties of electronic charge density are analysed by employing Bader’s atoms in molecules theory (AIM).