Microwave synthesis, crystal structure and spectroscopic investigations of 2-{[(2E)-(2-chlorobenzylidene) hydrazine] carbonyl} benzenesulfonamide and 2-({[(2E)-2-[4-(dimethylamino) benzylidene] hydrazine} carbonyl) benzenesulfonamide

摘要

The compounds 2-{[(2E)-(2-chlorobenzylidene) hydrazine] carbonyl} benzenesulfonamide 5a and 2-({[(2E)-2-[4-(dimethylamino)benzylidene] hydrazine} carbonyl) benzenesulfonamide 5b have been synthesized by microwave heating and characterized by NMR, FT-IR and single crystal X-ray crystallography. They have been obtained in higher yields in lesser reaction times through microwave irradiation. (C_(14)H_(12)ClN3O3S, 5a): MW = 337.782, triclinic, Pi, a = 7.8804(7) A, b = 11.5285(11) A, c = 18.1620 (19) A, α = 89.452(7)°, β = 76.847(8)°, γ = 75.999(8)°, V = 1557.2(3) A~3, Z = 4; (C_(17)H_(20)N4O4S, 5b): MW = 364.421, Orthorhombic, P2_12_12_1, a = 1,6.5693(2) A, b = 7.0856(3) A, c = 37.8187(15) A, α = 90°, β = 90°, γ = 90°, V = 1760.36(12) A~3, Z = 4. The delocalizations as well as the presence of the intra-molecular hydrogen bonding in 5a and 5b lead to the planarity of the benzene rings. There are π-π stacking interactions among the adjacent aromatic systems in both the compounds. It is also anticipated that the synchronized effect of both benzenesulfonamide and hydrazone groups in 5a and 5b should make them potential candidates for biological applications.