Crystal structure, conformation, vibration and optical band gap analysis of bis[rac-propranolol nitrate]

The crystal structure of the title rac-propranolol salt, C16H22NO2+ center dot NO3-, consists of two protonated propranolol residues and nitrate anions. Three virtually flat fragments, characteristics of most of the adrenolytics with oxy-methylene bridge are present in both the cations (A and B). The plane of the propranolol chain is twisted with respect to the plane of the aromatic ring in both the cations. Present study investigates the conformation and hydrogen bonding interactions, which play an important role in biological functions. A gauche conformation is observed for the oxo-methylene bridge of cation A, while a trans conformation prevails in cation B. These conformations are found in majority of beta-blockers. Presence of twenty intermolecular hydrogen bonds mediating through the anions stabilizes the crystal packing. Vibration analysis and earlier theoretical predictions complement the structure analysed. From the UV-Vis spectral analysis for the crystal, the optical band gap is found to be E-g = 5.12 eV, where as the chloride salt has E-g = 3.81 eV. The increase in the band gap may be attributed by the increase in the number of intermolecular hydrogen bonds. Good optical transmittance in the entire visible region and the direct band gap property suggest that it is a suitable candidate for optical applications in UV region. (C) 2009 Elsevier B.V. All rights reserved.