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) 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 R2<inf>2</inf> (8)rings. © TÜBİTAK, 2012.