H. Ünver, T. N. Durlu
Aug 13, 2003
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Journal
Journal of Molecular Structure
Abstract
Abstract 1-[N-(2-bromophenyl)]naphthaldimine (C17H12NOBr) (1) was synthesised and its crystal structure was determined. The compound 1 is orthorhombic, space group P212121 with a=12.653(2), b=13.7311(14), c=7.9799(12) A , V=1386.4(4) A 3 , Z=4, D c =1.563 g cm −3 , μ( Mo K α )=2.959 mm −1 , R=0.032 for 499 reflections I>2σ(I)]. There is an intramolecular hydrogen bond of distance 2.473(3) A between the hydroxyl oxygen atom and imine nitrogen atom, the hydrogen atom essentially being bonded to the oxygen atom. Minimum energy conformation was calculated as a function of torsion angle θ (C10–C11–N1–C12) varied every 5 degrees. The optimized geometry of the crystal structure corresponding to the non-planar conformation is the most stable conformation in all calculations. The results strongly indicate that the minimum energy conformation is primarily determined by hydrogen–hydrogen repulsions between the ortho-hydrogen atoms on the aldehyde rings. Complementary IR, 1H NMR and UV measurements in solution and in the solid state were carried out.