Constantinos D. Antoniadis, G. J. Corban, S. Hadjikakou
Apr 1, 2003
Citations
1
Influential Citations
56
Citations
Journal
European Journal of Inorganic Chemistry
Abstract
Direct reaction of 6-n-propyl-2-thiouracil (PTU), a widely used anti-thyroid drug against hyperthyroidism (Graves’ disease), or 5-chloro-2-mercaptobenzothiazole (CMBZTH) with iodine in a molar ratio of 1:1 resulted in the formation of the charge-transfer (CT) complexes [(PTU)I2] (1) or [(CMBZT)I2] (2). All reactions were carried out in dichloromethane and water solutions. Compounds 1 and 2 were characterized by elemental analyses, FT-Raman, FT-IR, UV/Vis and 1H NMR spectroscopy. The crystal structures of both complexes were determined by X-ray diffraction at 120(1) K (1) and 293(2) K (2). The charge-transfer nature of the bonds in the adducts 1 and 2 was verified by the lengthening of the I−I bond lengths as compared to the S−I bond lengths and by the characteristic CT bands observed in the UV spectra of the complexes. Compound 1 [(C7H10N2OS)I2] [monoclinic with space group P21/c and a = 9.8501(7), b = 10.3101(7), c = 12.0287(8) A, β = 99.707(6)°, Z = 4] consists of a propylthiouracil ligand bonded with an iodine atom through sulfur. Extended intermolecular N−H···O contacts link the molecules forming a supramolecular assembly. Compound 2 {(C7H4ClNS2)I2} [orthorhombic, space group P212121, a = 4.1650(10), b = 9.691(2), c = 28.471(6) A, Z = 4] consists of a 5-chloro-2-mercaptobenzothiazole ligand bonded with an iodine atom through sulfur. An extended intermolecular linkage via I···H−N bonds leads to the formation of an extended structure. Attempts to draw conclusions on the behavior of a thioamide — when used as an anti-thyroidal drug — towards iodine have been made. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)