Rearrangement and co-ordination of 1-[(4-methylphenyl)- sulfonamido]-2-[1-(2-pyridylmethylidene)amino]benzene

Abstract

Two different compounds, L¹ {3-[ethoxy(2-pyridyl)methyl]-1-[(4-methylphenyl)sulfonyl]-2-(2-pyridyl)-2,3-dihydro-1H-benzo[d]imidazole} and L² {1-[(4-methylphenyl)sulfonyl]-2-(2-pyridyl)-2,3-dihydro-1H-benzo[d]imidazole} have been synthesised by the reaction of 2-pyridinecarboxaldehyde with N-tosyl-1,2-diaminobenzene. L¹ was crystallographically characterised. The interaction of L¹ with a nickel centre was checked. Electrochemical interaction of Ni with L¹ and N-(2-hydroxyphenyl)salicylidenimine (H₂L⁴) produces NiL¹L⁴·2H₂O 1. Its recrystallisation in dichloromethane leads to the isolation of single crystals of NiL³₂·0.75H₂O 2 (HL³=1-[(4-methylphenyl)sulfonamido]-2-[1-(2-pyridylmethylidene)amino]benzene), where L¹ underwent a rearrangement. In the reaction of L¹ with Ni and p-toluenesulfonic acid in an electrochemical cell, complex 2 is isolated as the bulk product. Nickel complexes have been characterised by elemental analysis, IR spectroscopy and magnetic measurements. The molecular structure of 2 has been determined by single X-ray diffraction studies.