Crystal structure of N,N′-Bis-(2,5-dimethoxybenzylidene)-1,3-diaminopropane

Abstract

The Schiff-base compound N,N′-Bis-(2,5-dimethoxybenzylidene)-1,3-diaminopropan, (2,5-MeO-ba) 2 pn, is synthesized and characterized by elemental analysis, FT-IR and 1 H NMR spectroscopy. The crystal structure of (2,5-MeO-ba) 2 pn is determined by X-ray single crystal diffraction analysis. The X-ray diffraction analysis at 120 K reveals that (2,5-MeO-ba) 2 pn crystallizes in the orthorhombic system, Fdd2 space group with a = 29.339(9) Å, b = 29.4073(11) Å, c = 4.4524(2) Å, V = 3840.8(3) Å 3 , μ = 0.72 mm -1 , and Z = 8. Keywords: X-ray diffraction, orthorhombic symmetry, Schiff base.Schiff bases derived from substituted benzaldehyde [1-3] are widely used as chelating ligands forming transition metal complexes [4][5][6]. They have attracted considerable attention in the last years because the complexes are very interesting in many fields, such as catalysis [7] and magnetism [8]. Recently, several Schiff-base compounds with antibacterial activity have been investigated [9,10]. In this paper, the title compound (2,5-MeO-ba) 2 pn was synthesized and its molecular structure was characterized by elemental analysis, FT-IR and 1 H NMR spectroscopy, and X-ray structure analysis (Fig. 1).Experimental. All reagents and solvents for the synthesis and spectroscopic studies were commercially available and used as received without further purification. 1 H NMR spectra were measured with a BRUKER DRX-500 AVANCE spectrometer at 500 MHz and all chemical shifts are reported in δ units downfield from TMS. The infrared spectrum was recorded on a JASCO 680 plus FT-IR spectrophotometer as a KBr pellet.2,5-Dimethoxybenzaldehyde (0.332 g, 0.2 mmol) and 1,3-propanediamine (0.074 g, 0.1 mmol) were dissolved in ethanol (50 ml). The mixture was stirred at room temperature for 1 h to give a clear solution. Suitable crystals of the title compound (2,5-MeO-ba) 2 pn for the X-ray study were formed by slow evaporation of the solvent over 8 days at room temperature (yield 76%). The crystals are colorless. IR (KBr pellet, cm -1 ): 2829-3008 (m, C-H aromatic and aliphatic), 1638 Fig. 1. Chemical diagram of the title compound (2,5-MeO-ba) 2 pn.

Crystal Structures of Novel Bis-No-Acyclic Schiff Base Compounds

“…The methyl hydrogen atoms were allowed to rotate freely about the adjacent C-C bonds. The isotropic atomic displacement parameters of hydrogen atoms were set to 1.5U eq (C) for methyl groups and to 1. are consistent with the sp 2 hybrid character of C7 and N1 atoms [20][21][22][23][24][25]. There is one intramolecular hydrogen bond of the O-HѱN type in the compounds L 1 and L 2 ( Table 3).…”

“…Recently, our group has reported the syntheses and crystal structures of Schiff base compounds [ 4,[20][21][22][23][24][25]. Herein, we report the synthesis and the crystal structure determination of novel bis-NOacyclic Schiff base compounds, derived from 3-methoxy-4-(2-(4-formyl-2-ethoxyphenoxy)ethoxy)benzaldehyde with 2-aminophenol (L 1 ) or 4-aminophenol (L 2 ) (Scheme 1).…”

Untitled

“…The Schiff bases are one of the most important compounds that are not only used as ligand for preparation various coordination compounds with transition metal ions such as copper(I) [1][2][3], copper(II) [4,5], Ag(I) [1], Zn(II) [6][7][8], Hg(II) [9] and V(IV) [10], but also for various application and properties such as fluorescent pH prob [11], photoluminscent [12], detection of Fand AcO - [13], corrosion inhibition [14] and optical properties [15]. This is due to the fact that, Schiff base compounds are a) easily obtained by one-step procedure [16][17][18][19] b) the existence of tautomerization between phenol-imine and keto-amine form in Schiff bases derived from salicylaldehyde derivatives having 2-hydroxy group [20,21] and c) are prepared stable complexes [1][2][3][4][5][6][7][8][9][10]. Reimann et al [22] prepare water-soluble sulfonate Schiff base ligands and reported the fluorescent detectors of various for metal ions.…”