Synthesis and structural X-ray analysis of 1,1’-(naphthalene-1,8-diyl)-3,3’-dibenzoyl-bisthiourea and its use as anion-binding receptor

Abstract

A novel artificial receptor, 1,1‘-(naphthalene-1,8-diyl)-3,3‘-dibenzoyl-bisthiourea, based on a 1,8-naphthalene skeleton bearing bisthiourea groups was prepared and characterized by IR and 1H-NMR, 13C-NMR, and MS spectroscopic techniques. The compound proved to be an efficient and selective naked-eye detector for the fluoride, cyanide, and hydroxide ions in DMSO. The crystal structure of the title compound was examined by using X-ray crystallographic techniques and found to be crystallized in the monoclinic space group P − 1 with the unit cell parameters: a 8.1556(8) \AA, b 12.0127(11) \AA, c 13.2081(11) \AA, α 109.510(7) ◦ , ? 95.390(7)◦, ? 103.660(7)◦ , Z 2. The intramolecular N-H· · ·O hydrogen bondinginteractions between the N-H and the oxygen atom of CO groups support a 1,1‘-(naphthalene-1,8-diyl)- 3,3‘-dibenzoyl-bisthiourea framework. Moreover, the combinations of N—H· · ·S bonds produce R2_2 (8)rings.