Crystal Structure of N,N'-Bis(3-nitrobenzylidene)butane-1,4-diamine

Abstract

Schiff-bases are well-know chelating ligands in coordination chemistry. 1 During the last decade, Schiff-base complexes have been applied to catalytic reactions and biological systems. 2 Schiff bases can be used to obtain optical materials and conducting polymers. 3,4 Thus, new optical and organic conducting materials can be produced by using these compounds. These compounds, containing Schiff bases, seem to be suitable candidates for further chemical modifications, and may be used to produce optical communication and optical devices. 5 Recently, three Schiff-base compounds were reported with nitrobenzaldehyde, and have been structurally characterized. 6-8 In this research N,N′-bis(3-nitrobenzylidene)butane-1,4diamine was prepared by the reaction of butane-1,4-diamine (0.3 mmol, 27 mg) and 3-nitrobenzaldehyde (0.6 mmol, 91 mg), which were dissolved in chloroform (10 ml). The mixture was stirred at room temperature for 5 h (Fig. 1). Single crystals suitable for X-ray structure analysis could be obtained by crystallization from an ethanol and dichloromethane (1:1) solution, which afforded yellow crystals. The crystal and structure-refinement data are summarized in Tables 1-3. H atoms were placed at calculated positions, with C-H distances of 0.95-0.99 Å, and treated as riding atoms, with Uiso(H) = 1.3Ueq(C). In Fig. 1, two 3-nitrobenzaldehyde groups are bridged by butane-1,4-diamine via two C=N double bonds in a roughly linear geometry. This molecule is on the x61

Synthesis and Structural Characterization of (2E,3E)-N1,N2-Bis(4-chlorobenzylidene)ethane-1,2-diamine

“…1.4440 (7) N ( All the bond lengths and bond angles in the title compound are within normal ranges and comparable to those in the similar compounds 13,14,19 . The C7-N1 bond length of 1.268(8) Å, the C10-N2 bond length of 1.259(8) Å, the C23-N3 bond length of 1.280(8) Å and the C26-N4 bond length of 1.263(7) Å conform to the value for a double bond, while the C8-N1 bond length of 1.468(7) Å, the C9-N2 bond length of 1.440(7) Å, the C24-N3 bond length of 1.459(8) Å and the C25-N4 bond length of 1.459(8) Å conform to the value for a single bond.…”

“…The C7-N1 bond length of 1.268(8) Å, the C10-N2 bond length of 1.259(8) Å, the C23-N3 bond length of 1.280(8) Å and the C26-N4 bond length of 1.263(7) Å conform to the value for a double bond, while the C8-N1 bond length of 1.468(7) Å, the C9-N2 bond length of 1.440(7) Å, the C24-N3 bond length of 1.459(8) Å and the C25-N4 bond length of 1.459(8) Å conform to the value for a single bond. The C=N bond lengths are close to the corresponding bond length in N,N'-bis(3-nitrobenzylidene)butane-1,4-diamine [1.267(3) Å] 19 . The molecules are linked through C-H···Cl hydrogen bonds interactions ( Fig.…”

Schiff Bases as Potential Fungicides and Nitrification Inhibitors

“…Diaryl Methylene Diimines. Reaction of 2 equiv of aforesaid aromatic aldehydes with 1 equiv of 1,3-propyl/1,4-butyl/1,2cyclohexyl diamines separately in methanol resulted in diaryl methylene diimines (16)(17)(18)(19)(20)(21)(22)(23) in excellent yields (Figure 2), which were characterized using spectral techniques.…”

“…Compound 12 showed maximum ammonium-N retention with value 104 mg/ kg and significantly superior to others as evidenced from DMRT values. The next in performance were compounds 13,3,17,5,22,18,21,16,20 with 67-93 mg/kg ammonium-N. The rest of the compounds lay in the range of 24-64 mg/kg ammonium-N. From the overall performance it was found that the diimines (16)(17)(18)(19)(20)(21)(22)(23) showed moderate ammonium-N content (64-70 mg/kg) while monoimines showed low to high ammonium-N content (24-104 mg/kg).…”

Crystal Structure of N,N'-Bis(trans-cinnamaldehyde)ethylenediimine

“…[6][7][8][9] In the present work, we report on the crystal structure of another diimine Schiff base, viz. N,N′-bis(trans-cinnamaldehyde)ethylenediimine (ca2en) (Fig.…”