Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions - A Link between Ordinary Carbocations and Neutral Electrophiles

Mayer, Robert J.; Hampel, Nathalie; Mayer, Peter; Ofial, Armin R. und Mayr, Herbert (2019): Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions - A Link between Ordinary Carbocations and Neutral Electrophiles. In: European Journal of Organic Chemistry, Bd. 2019, Nr. 2-3: S. 412-421

Abstract

Optimized synthetic procedures for the straightforward access to eleven amino-substituted diarylmethylium tetrafluoroborates are described. These benzhydrylium ions cover a range of seven orders of magnitude in electrophilicity and provide a link between ordinary carbocations and neutral electrophiles. Five of these highly stabilized benzhydrylium tetrafluoroborates were characterized by single-crystal X-ray crystallography. While the experimentally determined bond lengths and angles in the solid state perfectly agree with those calculated by DFT methods for the gas phase and aqueous solution, crystal packing accounts for large differences in the twist angles of the aryl groups found in the solid state as compared to calculated structures.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1434-193X
• Sprache: Englisch