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Paper | Regular issue | Vol 65, No. 12, 2005, pp.2847-2860
Published online, 11th October, 2005
DOI: 10.3987/COM-05-10375
Crown Compounds Containing a 1,3,4-Thiadiazole Moiety: Microwave Assisted Synthesis, Crystal Structure and Quantum Calculations

Mounim Lebrini, Fouad Bentiss, Hervé Vezin, Jean Pierre Wignacourt, Pascal Roussel, and Michel Lagrenée*

*Laboratory of Cristallochemistry and Physicochemistry of the Solide, CNRS UMR 8012, ENSCL, BP. 90108, F-59652 Villeneuve d’Ascq Cedex, France

Abstract

A number of macrocyclic polyether compounds containing a 2,5-bis(2-hydroxyphenyl)-1,3,4-thiadiazole moiety are quickly prepared by a nucleophilic substitution reaction involving ethylene or polyethyleglycol ditosylate and a biphenol, the 2,5-bis(2-hydroxyphenyl)-1,3,4-thiadiazole, with solid anhydrous carbonate as a base under microwave irradiation. The quantum calculations at DFT level and the structure of different conformations of the 2,5-bis(2-hydroxyphenyl)-1,3,4-thiadiazole were performed both in vacuum and acetonitrile solvent using PCM method. The structures are ascertained by spectroscopic properties. The crystal structure of one of the crown compounds has been determined and shows the sufur atom to be inside the macroring cavity.