Ring Opening Reactions of β‐Propiolactam in Superacidic Media

Beck, Stefanie; Rück, Vanessa; Pietsch, Lea‐Viktoria; Jessen, Christoph und Kornath, Andreas J. (2022): Ring Opening Reactions of β‐Propiolactam in Superacidic Media. In: Chemistry – A European Journal, Bd. 28, Nr. 6

Abstract

The reaction of β-propiolactam in the superacidic systems HF/MF5 (M=Sb, As) led to the formation of monoprotonated 3-aminopropanoyl fluoride in the form of [C(O)F(CH2)2NH3][SbF6] and [C(O)F(CH2)2NH3][AsF6]. In the presence of traces of water, the diprotonated species β-alanine [C(OH)2(CH2)2NH3][AsF6]2 was synthesized for the first time. All salts were characterized by low-temperature infrared and Raman spectroscopy. Additionally, single-crystal X-ray analyses were conducted in the case of [C(O)F(CH2)2NH3][SbF6] and [C(OH)2(CH2)2NH3][AsF6]2. By using SO2 instead of HF as the solvent, the salt [C(OH)2(CH2)2NHSO][SbF6]2 was obtained, and single-crystal X-ray analysis of this salt containing a thionylimide moiety was conducted. For the formation of these open-chain compounds, an acyl cationic species as intermediate is assumed, which is formed from N-protonated β-propiolactam. Quantum chemical calculations at the B3LYP/aug-cc-pVTZ and MP2/aug-cc-pVTZ levels of theory were carried out to gain a better understanding of the formation and the structural properties of protonated β-propiolactam.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0947-6539
• Sprache: Englisch