Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin

Abstract

KEYWORDS(S)-5-Isopropyl-5-methyl-2-thiohydantoin was synthesized by one-pot reaction of α-methyl-Lvaline and thiourea in the absence of solvent. The crystal structure of this compound has been determined from single crystal X-ray diffraction data. This is the first report on the crystal structure of a homochiral 5-substituted 2-thiohydantoin with the unsubstituted NH groups. This compound, C7H12N2OS crystallizes in the chiral orthorhombic space group P212121 with four molecules in the unit cell. The unit cell parameters are: a = 8.2798(12) Å, b = 8.6024(13) Å, c = 12.826(2) Å and V = 913.6(2) Å 3 . In the crystals, the thioamide and amide N-H of one molecule are hydrogen-bonded to the thioamide C=S group of neighboring molecules to form rings with the R 2 2(8) graph-set motif, and these rings are linked into infinite one-dimensional tapes.Thiourea Homochiral Hydrogen-bond Crystal structure 2-Thiohydantoin 2-Thioxoimidazolidin-4-one

Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin

“…This unique structural feature endows the compounds with unique physicochemical and biological properties [14,15]. We have studied the crystal structures of a series of hydantoins and 2-thiohydantoins in order to get information on the factors controlling the molecular environment in the crystal [16][17][18][19][20][21][22].…”