Study of 5-azidomethyl-8-hydroxyquinoline structure by X-ray diffraction and HF–DFT computational methods

• Published in: Russian Journal of Physical Chemistry A Vol. 91; no. 2; pp. 358 - 365
• Main Authors: Bougharraf, H., Benallal, R., Sahdane, T., Mondieig, D., Negrier, Ph, Massip, S., Elfaydy, M., Lakhrissi, B., Kabouchi, B.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.01.2017; Springer Nature B.V; MAIK Nauka/Interperiodica
• Subjects: Charge transfer; Chemical Sciences; Chemistry; Chemistry and Materials Science; Cristallography; Crystal structure; Density functional theory; Energy gap; Hydrogen bonding; Hydroxyquinoline; Mathematical analysis; Molecular orbitals; Molecular structure; NMR; Nuclear magnetic resonance; Phase transitions; Physical Chemistry; Rietveld method; Single crystals; Solid phases; Structure of Matter and Quantum Chemistry; Thermal analysis; X ray powder diffraction; X-ray diffraction; X-ray diffraction; single crystal structure; HOMO‒LUMO; hydrogen bonding; HF‒DFT; 5-azidomethyl-8-hydroxyquinoline
• ISSN: 0036-0244; 1531-863X
• DOI: 10.1134/S0036024417020078

5-Azidomethyl-8-hydroxyquinoline has been synthesized and characterized using IR, 1 H and 13 C NMR spectroscopic methods. Thermal analysis revealed no solid-solid phase transitions. The crystal structure of this compound was refined by Rietveld method from powder X-ray diffraction data at 295 K. The single- crystal structure of the compound at 260 K was solved and refined using SHELX 97 program. According to the data obtained by both methods, the structure of the compound is monoclinic, space group P 2 1 / c , with Z = 4 and Z ' = 1. For the single crystal at 260 K, a = 12.2879 (9) Å, b = 4.8782 (3) Å, c = 15.7423 (12) Å, β=100.807(14)°. Mechanisms of deformation resulting from intra- and intermolecular interactions, such as hydrogen bonding, induced slight torsions in the crystal structure. The optimized molecular geometry of 5-azidomethyl-8-hydroxyquinoline in the ground state is calculated using density functional theory (B3LYP) and Hartree-Fock (HF) methods with the 6-311G( d,p ) basis set. The calculated results show good agreement with experimental values. Energy gap of the molecule was found using HOMO and LUMO calculation which reveals that charge transfer occurs within the molecule.