Protonated Ethylene Carbonate: A Highly Resonance-Stabilized Cation

Beck, Stefanie; Jessen, Christoph und Kornath, Andreas J. (2021): Protonated Ethylene Carbonate: A Highly Resonance-Stabilized Cation. In: Chemistryopen, Bd. 10, Nr. 12: S. 1160-1165

Abstract

Salts containing the monoprotonated ethylene carbonate species of were obtained by reacting it with the superacidic systems XF/MF5 (X=H, D;M=Sb, As). The salts in terms of [C3H5O3](+)[SbF6](-), [C3H5O3](+)[AsF6](-) and [C3H4DO3](+)[AsF6](-) were characterized by low-temperature infrared and Raman spectroscopy. In order to generate the diprotonated species of ethylene carbonate, an excess of Lewis acid was used. However, this only led to the formation of [C3H5O3](+)[Sb2F11](-), which was characterized by a single-crystal X-ray structure analysis. Quantum chemical calculations on the B3LYP/aug-cc-PVTZ level of theory were carried out for the [C3H5O3](+) cation and the results were compared with the experimental data. A Natural Bond Orbital (NBO) analysis revealed sp(2) hybridization of each atom belonging to the CO3 moiety, thus containing a remarkably delocalized 6 pi-electron system. The delocalization is confirmed by a C-13 NMR-spectroscopic study of [C3H5O3](+)[SbF6](-).

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 2191-1363
• Sprache: Englisch