Crystal Structure and Conformation of N-(5-Chlorosalicylidene)- 2-hydroxy-5-chloroaniline

Abstract

N-(5-Chlorosalicylidene)-2-hydroxy-5-chloroaniline was synthesized and its crystal structure determined. It crystallizes in the orthorhombic space group Pna21 with a = 14.668(4), b = 6.084(3), c = 27.980(4) Å , R = 0.051 for 4788 independent reflections). There are two independent nearly planar molecules in the asymmetric unit. The intramolecular hydrogen bonds occur between the pairs of atoms N1 and O1 [2.553(6) Å], N1 and O2 [2.585(5) Å], N2 and O3 [2.567(6) Å], N2 and O4 [2.620(5) Å], the hydrogen atoms essentially being bonded to the nitrogen atoms. The neighboring molecules are linked via an intermolecular O-H···O hydrogen bond [2.557(5) Å ]. Conformations of the title compound were investigated by semi-empirical quantum mechanical AM1 calculations. The optimized geometry of the molecular structure corresponding to the nearly planar conformation is the most stable conformation in the calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded steric interactions.

Bis[2-(cyclopropyliminomethyl)-5-methoxyphenolato]zinc(II)

“…In the field of coordination chemistry, they are used extensively as ligands due to intramolecular hydrogen bonds between O and N atoms, which is applicable for the formation of metal complexes. Schiff bases are also used in the field of photochromism and thermochromism in the solid state (Elerman et al, 2002). In this paper, we report the crystal structure of the title Schiff base compound.…”

Study on the nematicidal activity and chemical structure of NO bidentate Schiff base some metal complexes

“…Schiff bases are widely studied because of increasing recognition in biological systems . Schiff bases are the compounds containing azomethine group (−HC═N−), which play an essential role in the field of coordination chemistry . In recent years, there has been enhanced interest in the development of the chemistry of Schiff base ligands species as they readily form stable complexes with most of the transition metals .…”

Synthesis, Characterization and Antimicrobial Activities of Copper(II) Complexes of Schiff Base Ligand 2-[(3′-N-salicylidinephenyl)benzimidazole]

“…Transition metal complexes with 2-substituted benzimidazole ligands exhibit cytotoxic, antiviral and antiamoebic properties [2][3][4][5][6]. Schiff bases have the ability to reversibly bind oxygen, catalytic activity in the hydrogenation of olefins and exhibit photochromism and thermochromism [7] and hence have been used as ligands in coordination chemistry. Metal complexes of biologically important ligands are many a times more effective than uncoordinated N-heterocycles.…”