Synthesis, structural and computational studies of a novel anionic synthon and its derivatives

Abstract

A novel trimethylsilyl anionic synthon: 9-(4'-trimethylsilyl-1',2',3'-triazol-1'-yl)methylanthracene was synthesized by copper catalyzed reaction of 9- chloromethylanthracene, trimethylsilyl acetylene and sodium azide using dimethylformamide as solvent, in 95% yield. Good quality crystals obtained were subjected to X-ray diffraction studies and for the first instance of time, single crystal X-ray diffraction analysis of 9-(4'-trimethylsilyl-1',2',3'-triazol-1'-yl)methylanthracene is reported. The X-ray diffraction studies reveal that the compound crystallizes in monoclinic crystal system, with space group of P21/c. The molecular structure analysis show the anthracene- and triazolyl- ring systems being inclined to each other with a dihedral angle of 68.53(2)o. The crystal structure was governed by intermolecular C–H…N interactions. The intermolecular interactions were investigated by Hirshfeld surfaces and its related fingerprint plots indicate H...H interactions to be the predominant one towards the packing of three dimensional Hirshfeld surfaces. Also, the three dimensional interaction energies in a crystal were computed using energy model of B3LYP/6-31G(d,p) and their results showed that the dispersion energy components were dominated by electrostatic components. The density functional theory studies were carried out for the compound C20H21N3Si to investigate electronic properties, and chemical reactivity. Further, the novel compound was protodesilylated by potassium fluoride in methanol solvent to obtain 9-(1',2',3'-triazol-1'-yl)methylanthracene, in 94% yield. Novel 9-(1',2',3'-triazol-1'-yl)methylanthracene was subjected to molecular docking and corrosion inhibitory studies.