New examples of N(+)–H⋯(−)S hydrogen bonds: Synthesis and X-ray study of selected secondary ammonium tri-tert-butoxysilanethiolates

Tri-tert-butoxysilanethiol reacts with secondary amines: diethylamine, morpholine, dicyclohexylamine and 2,2,4,4-tetramethylpiperidine yielding appropriate ammonium salts. Structures of the products have been studied by X-ray diffraction. All the compounds form dimeric units in the solid state. Their common feature is a central core formed by four charge-assisted N(+)–H⋯(−)S hydrogen bonds in the form of eight-membered ring with four donors and two acceptors.

Anionic sulfur atom, from tri-tert-butoxysilanethiolate anion, was utilised as an acceptor in charge-assisted hydrogen bonding of the N(+)–H⋯S(−) type. Hydrogen bonds form an eight-membered ring with four donor and two acceptor atoms in all ammonium salts studied.Figure optionsDownload as PowerPoint slide