Structural and spectral studies of N-2-(pyridyl)-, N-2-(4-, 5-, and 6-picolyl)- and N-2-(4,6-lutidyl)- N′-2-methoxyphenylthioureas

• Published in: Journal of molecular structure Vol. 562; no. 1; pp. 95 - 105
• Main Authors: West, Douglas X., Swearingen, John K., Hermetet, Ann K., Ackerman, Lily J.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 02.05.2001
• Subjects: 2-methoxyphenylthioureas; Bifurcated hydrogen bonding; Crystal structures; Heterocyclic thioureas; Crystal structures; Bifurcated hydrogen bonding; Heterocyclic thioureas; 2-methoxyphenylthioureas
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/S0022-2860(00)00824-3

N-2-(pyridyl)- N′-2-methoxyphenylthiourea, PyTu2OMe, monoclinic, C2/ c, a=15.727(3), b=11.251(2), c=15.026(4) A ̊ , β=104.78(2)°, V=2570.9(2) A ̊ 3 and Z=8; N-2-(4-picolyl)- N′-2-methoxyphenylthiourea, 4PicTu2OMe, orthorhombic, Pbca, a=11.439(9), b=15.897(6), c=14.920(6) A ̊ , V=2713.0(4) A ̊ 3 and Z=8; N-2-(5-picolyl)- N′-2-methoxyphenylthiourea, 5PicTu2OMe, triclinic, P-1, a=7.586(2), b=8.505(3), c=11.308(5) A ̊ , α=73.29(3), β=89.04(3), γ=83.38(3)°, V=694.0(6) A ̊ 3 and Z=2; N-2-(6-picolyl)- N′-2-methoxyphenylthiourea, 6PicTu2OMe, monoclinic, P2 1/ c, a=11.372(4), b=15.808(4), c=16.141(7) A ̊ , β=102.96(3)°, V=2827.8(3) A ̊ 3 and Z=8 and N-2-(4,6-lutidyl)- N′-2-methoxyphenylthiourea, 4,6LuTu2OMe, monoclinic, P2 1/ n, a=7.546(4), b=23.400(5), c=8.927(5) A ̊ , β=109.42(5)°, V=1486.7(2) A ̊ 3 and Z=4. Some of these molecules have a bifurcated intramolecular hydrogen bond between N′H and the pyridyl nitrogen and the 2-methoxy oxygen, and all have intermolecular hydrogen bonding between NH and a thione sulfur of a second molecule to form centrosymmetric dimers. Solution 1H NMR studies (CDCl 3) show the N′H resonance considerably downfield for each thiourea and its position, as well as that of NH, is affected by substituents on the pyridyl ring.