Synthesis, Spectroscopic Characterization, X-Ray Structure and DFT Studies on 4-(2-Hydroxyphenyl)-4,5,6,7-Tetrahydro-1H-Imidazo[4,5-c]pyridin-5-ium Chloride Hydrate

Abstract

The title molecular salt, 4-(2-hydroxyphenyl)-4,5,6,7-tetrahydro-1H- imidazo[4,5-c]pyridin-5-ium chloride hydrate (C <inf>12</inf>H <inf>14</inf>N <inf>3</inf>O +·Cl·H <inf>2</inf>O), was synthesized and characterized by IR-NMR spectroscopy and single-crystal X-ray diffraction. In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies and gauge-independent atomic orbital (GIAO) 1H and 13C NMR chemical shift values of the title compound in the ground state have been calculated using the density functional theory (DFT/B3LYP) method with the 6-31++G(d,p) and 6-311++G(d,p) basis sets, and compared with the experimental data. Besides, molecular electrostatic potential (MEP) distribution and non-linear optical properties of the title compound were investigated by theoretical calculations at the B3LYP/6-311++G(d,p) level. © 2011 Elsevier B.V. All rights reserved.