Roesky's Ketone, Structure aromaticity and Reactivity

The molecular and crystal structure of the title compound, 5-oxo-1,3,2,4-dithiadiazole or Roesky's ketone (1), is studied experimentally by re-determining the crystal structure and theoretically by calculations at the density functional level of theory using an extended basis set. A comprehensive set of properties, consisting of orbital topologies, atomic charges, atomic and molecular dipoles, aromaticity parameters and Fukui functions of the title compound and a number of its constitutional isomers was calculated in order to formulate a description of its structure, its aromaticity and reactivity. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.