SYNTHESIS, CHARACTERIZATION, AND X-RAY CRYSTALLOGRAPHIC STRUCTURE OF 1,3-DIMETHYL-2(3H)-IMIDAZOLESELONE

The reaction of elemental Se with 1,3-dimethylimidazolium iodide in methanolic K2CO3 yields 1,3-dimethyl-2(3H)-imidazoleselone for which three addition products, two with bromine and one with iodomethane, have been synthesized and for which X-ray crystallographic analysis shows the structure to consist of a selenium-substituted planar heterocyclic ring with bond distances and angles significantly different from those noted for the previously reported sulfur analog [1,3-dimethyl-2(3H)-imidazolethione, dmit]. Crystal data: C5H8N2Se, space group C mcm, M = 175.03, a = 8.625(3), b = 11.447(6), c = 6.900(4) angstrom, V = 681.24 angstrom3, Z = 4, D(c) = 1.707 g cm-3, D0 = 1.68 g cm-3, lambda = 0.71073 angstrom (Mo-K(alpha)), mu = 5.35 mm-1, R = 0.034, and R(w) = 0.031.