Synthesis and structural and vibrational analysis of (5,7-dichloro-quinolin-8-yloxy) acetic acid

E. ROMANO, M. V. CASTILLO, J. L. PERGOMET, J. ZINCZUK, S. A. BRANDÁN

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2012 vol. 1018 p. 149 - 155

0022-2860

We have prepared the (5,7-dichloro-quinolin-8-yloxy) acetic acid and characterized it by infrared andRaman spectroscopies in the solid phase and by nuclear magnetic resonance (NMR) spectroscopy in aCDCl3 solution. The density functional theory (DFT) together with the 6-31G and 6-311++G basis setswere used to study its structure and vibrational properties. Two stable conformations of the compoundwere theoretically determined in the gas phase and probably these conformations are present in the solidphase. The harmonic vibrational wavenumbers for the optimized geometries were calculated at the sametheory levels. For a complete assignment of all the observed bands in the vibrational spectra the DFT calculationswere combined with Pulay’s scaled quantum mechanical force field (SQMFF) methodology inorder to fit the theoretical wavenumber values to the experimental ones. The force constants for the(5,7-dichloro-quinolin-8-yloxy) acetic acid were calculated and compared with those obtained for the(5-chloro-quinolin-8-yloxy) acetic acid and 2-(quinolin-8-yloxy)-acetic acid compounds. Furthermore,the characteristics of the electronic delocalization, the topological properties of the electronic charge densitytogether with the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital(LUMO) energy gaps were studied