Synthesis, spectroscopic characterization, X-Ray analysis, and DFT-HF calculations of 5-ethoxymethyl-8-hydroxyquinoline

Abstract

5-ethoxymethyl-8-hydroxyquinoline was synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR). The crystal structure determined at room temperature (295 K) by means of X-ray powder diffraction is orthorhombic, with space group Pbca and eight molecules per unit cell (Z = 8, Z′ = 1). The lattice parameters are: a = 7.9551(12) Å, b = 17.981(3) Å, c = 15.125(2) Å and V = 2163.5(6) Å3. Geometric parameters and properties depending on the charge distribution around the different types of donors and acceptors bonds within the molecule are calculated by density functional theory (DFT/B3LYP) and Hartree–Fock methods. Atomic charges and dipole moment value permit qualitative predictions about high reactivity of this molecule. The 5-ethoxymethyl-8-hydroxyquinoline adopts a non-planar structure in the solid state and the molecule is stabilized by contact system as π–π stacking interactions, weak intra and intermolecular H-Bonding O–H···N and C–H···O types, this latter involving the rings of both adjacent molecules in plans with a gap from 0.638 Å.