Study of Hydrogen Bonds in Crystalline 5-Nitrouracil. Density Functional Theory Calculations of the O-17, N-14, and H-2 Nuclear Quadrupole Resonance Parameters

M. Mirzaei and N.L. Hadipour*

Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

Hydrogen bond interaction properties of backbone uracil was studied in crystalline structure of 5-nitrouracil. To this aim the electric field gradient tensors were calculated at the level of density functional theory in two single (non-hydrogen bonded) and cluster (hydrogen-bonded four-molecule) models of 5-nitrouracil. The electric field gradient tensors at the sites of O-17, N-14, and H-2 nuclei were converted to the experimentally measurable nuclear quadrupole resonance spectroscopy parameters, quadrupole coupling constant and asymmetry parameter. The results indicated different hydrogen bond interaction properties at the sites of various nuclei and also the protective role of -NO₂ group for contribution of O1 to hydrogen bond interactions in comparison with uracil. The density functional theory calculations were performed using GAUSSIAN 98 package employing B3LYP method and 6-311G** and 6-311++G** basis sets.

Keywords: 5-Nitrouracil, Hydrogen bond, Nuclear quadrupole resonance, Density functional theory, Electric field gradient tensors