Acyl fluorides and acyl cations represent typical reactive intermediates in organic reactions, such as Friedel-Crafts acylation. However, the comparatively stable phenyl-substituted compounds have not been fully characterized yet, offering a promising backbone. Attempts to isolate the benzoacylium cation have only been carried out starting from the acyl chloride with weaker chloride-based Lewis acids. Therefore, only adducts of 1,4-stabilized acyl cations could be obtained. Due to the low melting point of benzoyl fluoride, together with its volitality and sensitivity toward hydrolysis, the structures of the acyl fluoride and its acylium cation have not been determined. Herein, we report the first crystal structure of benzoyl fluoride, CHFO or PhCOF (monoclinic P2/n, Z = 8) and the benzoacylium undecafluorodiarsenate, CHO·AsF or [PhCO][AsF] (monoclinic P2/n, Z = 4). The compounds were characterized by low-temperature vibrational spectroscopy and single-crystal X-ray analysis, and are discussed together with quantum chemical calculations. In addition, their specific π-interactions were elucidated.
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http://dx.doi.org/10.1107/S2053229625000476 | DOI Listing |
Acta Crystallogr C Struct Chem
February 2025
Department Chemie, Ludwig-Maximilians Universität, Butenandtstrasse 5-13 (Haus D), D-81377 München, Germany.
Acyl fluorides and acyl cations represent typical reactive intermediates in organic reactions, such as Friedel-Crafts acylation. However, the comparatively stable phenyl-substituted compounds have not been fully characterized yet, offering a promising backbone. Attempts to isolate the benzoacylium cation have only been carried out starting from the acyl chloride with weaker chloride-based Lewis acids.
View Article and Find Full Text PDFChem Asian J
November 2024
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078, USA.
The germylamine PhGeN(SiMe) was synthesized from PhGeCl and LiN(SiMe) and its X-ray crystal structure was determined. This structure represents only the fourth crystallographically characterized germylamine that has been reported. The two sterically encumbering -SiMe groups completely encapsulate the germanium-nitrogen bond and the geometry at the nitrogen atoms is trigonal planar rather than pyramidal.
View Article and Find Full Text PDFOrg Lett
March 2024
School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, Anhui 230000, China.
An intermolecular Suzuki-Miyaura-type reaction of benzoyl fluorides with alkyl boronic acids to synthetic ketone was revealed by cooperative -heterocyclic carbene (NHC) and photoredox catalysis. Various alkyl boric acids can be converted into alkyl radicals without external oxidants or activators. Moreover, the catalytic system was feasible for the difunctionalization of styrenes via a radical relay process.
View Article and Find Full Text PDFAnal Chem
July 2023
Department of Chemistry, Washington University in St. Louis, St. Louis, Missouri 63130, United States.
Protein footprinting mass spectrometry probes protein higher order structure and dynamics by labeling amino acid side-chains or backbone amides as a function of solvent accessibility. One category of footprinting uses residue-specific, irreversible covalent modifications, affording flexibility of sample processing for bottom-up analysis. Although several specific amino acid footprinting technologies are becoming established in structural proteomics, there remains a need to assess fundamental properties of new reagents before their application.
View Article and Find Full Text PDFChem Sci
March 2023
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road Chengdu 610064 P. R. China
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