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

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, 13 C-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) Å, b = 12.0127(11) Å, c = 13.2081(11) Å, α = 109.510(7) ◦ , β = 95.390(7) ◦ , γ = 103.660(7) ◦ , Z = 2. The intramolecular N-H· · ·O hydrogen bonding interactions between the N-H and the oxygen atom of C=O groups support a 1,1’-(naphthalene-1,8-diyl)- 3,3’-dibenzoyl-bisthiourea framework. Moreover, the combinations of N—H· · ·S bonds produce R^2 2 (8)rings.