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 H-1-NMR, C-13-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) angstrom, b = 12.0127(11) angstrom, c = 13.2081(11) angstrom, alpha = 109.510(7)degrees, beta = 95.390(7)degrees, gamma = 103.660(7)degrees, Z = 2. The intramolecular N-H center dot center dot center dot 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 center dot center dot center dot S bonds produce R-2(2) (8) rings.