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

• Published in: Spectroscopy letters Vol. 42; no. 2; pp. 73 - 80
• Main Authors: Kunimoto, Ko-Ki, Ichitani, Masaki, Ogawa, Toshikazu, Kitoh, Soh-ichi, Kuwae, Akio, Hanai, Kazuhiko
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01.03.2009
• Subjects: 1-acetyl-5-benzyl-2-thiohydantoin; 5-benzyl-2-thiohydantoin; ab initio MO calculation; crystal structure; molecular conformation; vibrational spectra
• ISSN: 0038-7010; 1532-2289
• DOI: 10.1080/00387010802428575

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 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.