Structural and spectral studies of N-2-(4,6-lutidyl),N'-tolylthioureas

Article abstract of DOI:10.1016/S0022-2860(99)00314-2

N-2-(4,6-lutidyl)-N'-o-tolylthiourea, 4,6LuTuoT, triclinic, P-1, a = 7.470(2), b = 9.799(5), c = 10.269(3) ?, α = 90.514(4), β = 98.89(3), γ = 90.14(3)°, V = 742.5(9) ?³, Z = 2, μ = 2.09 mm^-1; N-2-(4,6-lutidyl)-N'- m-tolylthiourea, 4,6LuTumT, monoclinic, P2₁/a, a = 7.2393(2), b = 16.636(3), c = 12.557(1) ?, β = 101.968(9)°, V = 1479.4(6) ?³, Z = 4, μ=2.10mm^-1 and N-2-(4,6-lutidyl)-N'-p-tolylthiourea, 4,6LuTupT, triclinic, P-1, a=7.883(2), b=7.9024(8), c = 23.273(4) ?, α = 86.49(1), β = 86.48(2), γ = 88.45(2)°, V = 1443.9(7) ?³, Z = 4, μ = 2.15 mm^-1. These molecules have an intramolecular hydrogen bond between N'H and the pyridyl nitrogen, as well as intermolecular hydrogen bonding between NH and a thione sulfur of a second molecule to form centrosymmetric dimers. Solution ¹H NMR studies (CDCl₃) show the N'H resonance considerably downfield for each thiourea and its position, as well as that of NH, are affected by substituents on the phenyl ring. (C) 2000 Elsevier Science B.V.