Abstract

Reaction of NioylH and CuoylH with the diazonium salt of sulfanilic acid quantitatively produces diaza complexes by coupling at the C-12 position. X-ray structural study: [Nioyl–N=N–C6H4SO3H]·H2O; C19H28O6N6S1Ni1 M r = 527.23, monoclinic P21/c, a = 12.752(3), b = 10.795(3), c = 16.609(3) A, β = 92.46(3)°, V = 2284.2(9) A3, Z = 4, D x = 1.533(2) mg m−3 [Cuoyl–N=N–C6H4SO3H]· HCl ·3H2O; C19H33O8N6S1Cu1Cl1, M r = 604.56, triclinic, $${P\bar 1}$$ , a = 8.4019(8), b = 11.2266(99), c = 14.9370(20) A, α = 84.264(7), β = 75.309(8), γ = 73.024(8)°, V = 1303.0(2) A3, Z = 2, D x = 1.541(2) mg m−3. The complexes were isolated from about 0.2 M HCl and had different formulas due to differing protonation. The sulfonic acid proton resides on the diaza nitrogen attached to the C6H4 ring and with the copper(II) analogue, protonation also occurs on the intramolecular hydrogen-bond oxygen. Bond distance and angle comparisons are made and related to potential electron delocalization between aromatic rings.

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