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Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V)

Sandro Hollenstein ; Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule Zürich, ETH-Zentrum, Universitatstrasse 16, CH-8092 Zürich, Switzerland
Christian Lohse ; Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule Zürich, ETH-Zentrum, Universitatstrasse 16, CH-8092 Zürich, Switzerland
Thomas Laube ; Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule Zürich, ETH-Zentrum, Universitatstrasse 16, CH-8092 Zürich, Switzerland

Puni tekst: engleski, pdf (22 MB) str. 727-736 preuzimanja: 126* citiraj
APA 6th Edition
Hollenstein, S., Lohse, C. i Laube, T. (1992). Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V). Croatica Chemica Acta, 65 (3), 727-736. Preuzeto s https://hrcak.srce.hr/137130
MLA 8th Edition
Hollenstein, Sandro, et al. "Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V)." Croatica Chemica Acta, vol. 65, br. 3, 1992, str. 727-736. https://hrcak.srce.hr/137130. Citirano 05.03.2021.
Chicago 17th Edition
Hollenstein, Sandro, Christian Lohse i Thomas Laube. "Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V)." Croatica Chemica Acta 65, br. 3 (1992): 727-736. https://hrcak.srce.hr/137130
Harvard
Hollenstein, S., Lohse, C., i Laube, T. (1992). 'Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V)', Croatica Chemica Acta, 65(3), str. 727-736. Preuzeto s: https://hrcak.srce.hr/137130 (Datum pristupa: 05.03.2021.)
Vancouver
Hollenstein S, Lohse C, Laube T. Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V). Croatica Chemica Acta [Internet]. 1992 [pristupljeno 05.03.2021.];65(3):727-736. Dostupno na: https://hrcak.srce.hr/137130
IEEE
S. Hollenstein, C. Lohse i T. Laube, "Crystal Structure Analysis and NMR Spectra of N-(Pentafluorobenzoyl)-4-dimethylaminopyridinium Hexachloroantimonate(V)", Croatica Chemica Acta, vol.65, br. 3, str. 727-736, 1992. [Online]. Dostupno na: https://hrcak.srce.hr/137130. [Citirano: 05.03.2021.]

Sažetak
The crystal structure analysis of N-(pentafluorobenzoyl)-4-dimethyl- aminopyridinium hexachloroantimonate(V) (space group: PI, measurement at -80 °C; high-order refinement; R = 0.035, Pw = 0.035 with all data) shows, that the carbonyl group and the dimethylaminopyridine (DMAP) fragment have a practically coplanar arrangement, while the pentafluorophenyl group is twisted b yea. 69° out of that plane. The resulting CO-DMAP-TT-interaction allows a charge delocalization towards the dimethylamino group, i.e. the cation may be best described as an iminium ion. The crystal packing reveals cation-anion interactions only in the formal iminium fragment. The carbonyl-C atom, which is attacked by a nucleophile in the course of an acylation reaction, has two intramolecular and one intermolecular van der Waals contacts to fluorine atoms. The structure is also interpreted in terms of a beginning dissociation into an acyl cation and DMAP. The 'H, 13C and 19F NMR spectra are compared with those of related molecules.

Hrčak ID: 137130

URI
https://hrcak.srce.hr/137130

Posjeta: 275 *