Crystal Structures and Conformations of 5-Benzyl-2-thiohydantoin and Its 1-Acetylated Derivative

Abstract

Abstract:The crystal structures of 5-benzyl-2-thiohydantoin (5-BTH) and 1-acetyl-5-benzyl-2-thiohydantoin (1-Ac-5-BTH) have been determined by X-ray diffraction. In the 5-BTH crystals, the enantiomeric (R)-and (S)-5-BTH molecules are connected to form cyclic dimers via the hydrogen bonds of the thioamide and the amide moieties. On the other hand, the intermolecular hydrogen bonds in 1-Ac-5-BTH crystals form an infinite chain. These differences 1 SpectroscLett_kunimoto_revised in the hydrogen bond pattern are also discussed in the IR and Raman spectra. The ab initio molecular orbital calculations (Gaussian 03) with 6-31G(d,p) basis set were carried out for 5-BTH and 1-Ac-5-BTH to get the preferred conformation.

Experimental and computational study of the energetics of hydantoin and 2-thiohydantoin

“…Our results are in a very good agreement with the experimental observations of several hydantoin and 2-thiohydantoin derivatives [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61].…”

A New Polymorph of 2-Thiohydantoin

“…We have been studying the crystal structures and conformations of 5-substituted-2-thiohydantoins and their derivatives. 2 During the course of a crystallization experiment, we obtained a crystal modification of 2-thiohydantoin (TH) that is different from the previously reported form. 3,4 In this paper, we report on the crystal structure of a new polymorph of TH (I, see Figs.…”

rac-5-(1-Methylethyl)-2-sulfanylideneimidazolidin-4-one

“…For the biological activity of 2-thiohydantoin derivatives, see: Ghoneim et al (1987); Marton et al (1993). For the crystal structures of related compounds, see: Kunimoto et al (2009); Ogawa et al (2007). For details of the synthesis, see: Wang et al (2006).…”